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Holiday Rentals near Southernmost Point

Whitehead Street, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach1 / 19
    (1)Excellent
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Shipyard-1/2 Block Duval Street1 / 9
    (1)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (9)Excellent
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Studio Blu1 / 15
    (1)Excellent
    1.0 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    We stayed at Blue on White Jan-Mar of 2017 and couldn't have been happier with our choice! The apartment is cozy (it is a studio) but at the same time is well maintained and...
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    About this property
    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this nightly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided! This property will meet all of the demands a...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    ** Fantastic Spring& Summer  Stay Downtown walk everywhere **1 / 36
    (5)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 25 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
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    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Conch Haven Old Town 1/1 MONTHLY Rental1 / 16
    (5)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Porch
    • Balcony
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2020
    We have been spending at least a month in Key West every winter for 6 years, usually on our boat. This year we rented this property and really enjoyed it. It is furnished with...
    Reviewed 23 September 2019
    Two months is not enough for me, would like to live there.This is my second year I stay at this house with family visiting couple of times.The owners Stephanie an Donna are...
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location1 / 28
    (3)Excellent
    1.0 kilometres from Southernmost Point
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
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    Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2018
    Great location!!! They supplied many extras beach chairs and beach towels. Loved that they had bikes right at the condo. We would definitely book this condo again
    Reviewed 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    STOP-LOOK NO FURTHER!!3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIF1 / 41
    (16)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Balcony
    • Waterfront
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2020
    This condo in the Shipyard Condominiums was a perfect location for us. We went to get away from Missouri winter weather and to attend Mile0fest. We could walk to the Green...
    Reviewed 18 September 2019
    The owners, Ed & Kerry are tremendous people to work with. I will definitely book their condo again. They are a 5 star operation. Thank you for a wonderful experience.
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    About this property
    Billy's Blue Heaven is fresh, clean and Pristine. Our condo includes one parking spot for an automobile directly in front of our condo. We're just a two minute walk to Duval Street and only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex 's lush...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (83)Excellent
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2020
    We stayed at Casa Del Sol over New Year's Eve as a family of 4. The townhouse was just as advertised, well appointed in a wonderful location. The weather was beautiful and we...
    Reviewed 29 December 2019
    The location is fantastic. It is walking distance from so many restaurants, places to see and of course Duvall St. which is only 2-3 blocks away. The condo is beautiful. From...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.1 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here your vacation dreams come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 57
    (41)Excellent
    0.1 kilometres from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2019
    I stayed here with a group of 10 friends. 4 couples and three singles. We had the best time. The house is beautiful. The pool amazing. Abby was responsive and helpful. Our...
    Reviewed 20 June 2018
    This place has everything you could need and want while you stay in Key West. Conveniently located near restaurants, attractions and things to do. Very happy with Seaside Place!
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Sunny View1 / 24
    (2)Excellent
    0.7 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2014
    The property was exactly as described and in tiptop shape. Everything was ready for our stay, the house was comfortable and a fair value.Also, the folks from at Home in Key...
    Reviewed 10 February 2011
    We had a wonderful time. The weather was great. The cottage was in the perfect location, very clean and filled with everything we needed. It was better than the condo we had...
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    About this property
    Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street. Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental Key West perfect escape for a couple or singles looking to get away from it all in...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    President's Walk1 / 26
    (1)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This place was perfect for the three adults and infant. The proximity to the pool, Duval St., and Green Parrot really made this beautiful condo ideal for a long Key West trip...
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    About this property
    It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community pools in the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 46
    (9)Excellent
    0.9 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2019
    Key West Oasis is a perfect warm weather get-a-way with a very private (no view of neighbors) backyard and an enclosed outdoor shower as a plus! The house was recently renovated...
    Reviewed 27 February 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Parking
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer. Located in the exclusive gated community of the Truman Annex, this...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Bayview Harbor1 / 24
    (1)Average
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Parking
    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2019
    This unit was nice and well maintained. We enjoyed sitting out on the front porch in the morning greeting people walking or bike riding by. FYI there is no oven. Sometimes...
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    About this property
    Looking for a peaceful retreat yet close to everything? Ideally located on Southard Street, within walking distance to the beach at Fort Zachary Taylor State Park, Duval Street and Mallory Square, Bayview Harbor is the spot you’ve been looking for. This unique property is newly renovated to...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    0.9 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfect spot offers plenty of private outdoor space within walking distance of great restaurants and shops. Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded community surrounded by lush tropical...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    0.4 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Parking
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Casa Grande1 / 25
    (5)Excellent
    0.3 kilometres from Southernmost Point
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2018
    5 couples, one house, and we could not have asked for more. Everyone had their own space and tons of space to share. The pool was amazing, the house was clean. Everyone loved...
    Reviewed 6 May 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard...
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    About this property
    Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions! CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 27
    (2)Excellent
    0.8 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2017
    We have stayed here 2 or 3 times. It is small, but there are just 2 of us and our dog. Works for us! Very cute and cozy. Washer & dryer. Compound is quiet and...
    Reviewed 13 August 2016
    The Cigar House has one the best location you can expect in Key West, close to Fort Zachary, Hemingway's House or Duval St. and all its attractions.This lovely house is full of...
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    About this property
    OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    1.2 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool. Awaken your senses with tropical breezes, turquoise waters and Key West Sunshine in this brand new 2-bedroom, den, 3-bath home. A secluded location yet the best of both worlds allows...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home. This tropically inspired three level property has all the updated amenities for you and your guests to enjoy, plus be within walking distance of the Southernmost Point, the Hemingway...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 21
    (6)Very good
    0.8 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2019
    A perfect stay for myself, my husband and 12 year old son; we wished we could have stayed longer and would love to return! A meticulously clean and hip home with an airy...
    Reviewed 28 June 2019
    Pros: Cute cottage in a great central location to Duval, Hemingway house, fort Zachary. Adequate dishes and pans to cook with though could use pizza cutter. Owner included...
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    About this property
    OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (2) queen beds, and (1)...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Duval Breeze1 / 24
    (57)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 February 2020
    Location is great, very convenient. Unit was super clean. Rented for two weeks. On day six parking pass was lost,called AT HOME AT KEY WEST. At this time I was asked if they...
    Reviewed 6 July 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
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    About this property
    Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches! Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Mermaids House, Historic Old Town Key West1 / 38
    (36)Excellent
    0.7 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    Reviewed 18 December 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Emma's Escape1 / 23
    (4)Excellent
    0.8 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2013
    We have been staying at 717a Emma for four years now. We started for one month and next year, we'll be there for three. I think that this property has one of the most amazing...
    Reviewed 6 February 2013
    Once again we enjoyed our winter stay in Key West. The climate in the main attraction, but Key Westalso full of interesting people and places. The condo became a home away...
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    About this property
    Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street. Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Finn Key1 / 24
    (33)Very good
    0.9 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    I traveled with my best friend and her husband to Key West, and we decided on renting Finn Key for about a week. The location was phenomenal - we barely needed the car! We could...
    Reviewed 11 February 2016
    Lovely condo,great location, have stayed at Truman many times. Condo is clean and comfortable, neighbors upstairs must live here full time, they walk a little heavy but I...
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    About this property
    Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat! A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    ** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **1 / 27
    (13)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 19 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    City Cay1 / 23
    (4)Very good
    1.0 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    We stayed for a week at City Cay. The location could not have been any better. The condo was supper clean and well maintained. We would definitely stay here again! It is a one...
    Reviewed 2 August 2016
    We loved City Cay. It was a small condo with one king bed, a futon and a small kitchen, but it was exactly what we needed. The bed was super comfortable. The bathroom was...
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    About this property
    Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level condo that has been meticulously renovated and furnished in a sleek modern style of the hippest urban...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Crowner's Jewel1 / 24
    (35)Very good
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2017
    Stayed recently for a week and while the condo was clean and well maintained , and the location was great the showers were just way too small. There are two bathrooms upstairs...
    Reviewed 5 November 2014
    Great Place! 2 blocks from Duval. Spacious, great amenities. Showers are tiny but at least there are 2 which helps bigger groups get ready. Clean. Nice neighborhood.
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    About this property
    Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem! Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.0 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West. For anyone with an affinity for the sea, everywhere you turn is a reminder of the water – from sailboat replicas of every shape and size; prints of fish and sailor...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Verandah1 / 24
    (11)Very good
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2012
    We enjoyed everything about our wonderful home in Key West. We felt right at home, great location, we could walk everywhere, short drive to the beach, harbor, and restaurants...
    Reviewed 2 September 2011
    Everything was great about my stay. At Home Key West is great to work with and very easy to get in touch with should an issue arise. The location of this house is great, and...
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    About this property
    A beautifully designed yet comfortable private home that you may never want to leave, only to go outside to your private pool and secluded space to hang out - that's the Verandah! Tucked away on historic Frances Street lies your island escape. This stunning monthly vacation rental offers two...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Linger Longer1 / 26
    (22)Very good
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived...
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    About this property
    Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation! Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    A Barefoot Retreat1 / 27
    (1)Very good
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect home away from home? No need to look any further! No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community. This two-bedroom, one bath, upper floor condo will feel like your own tropical home the minute you...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.9 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Terrace
    • Balcony
    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space. It is rare to find a true jewel like Tropical Casita, nestled in a sweet little spot amid lush landscaping and secluded tranquility....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    1.2 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
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    • Washer
    • Balcony
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military Hospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    A Place In Paradise1 / 24
    (23)Very good
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2017
    The townhouse is in the perfect location. Close to everything. The community is very clean and quiet and the pool, albeit small, was great and just around the corner...
    Reviewed 13 November 2013
    I've been going to KW every year for about a decade and have learned that your home base for the week can be the difference between a good trip and a truly great trip. I've...
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    About this property
    Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (3)Very good
    0.8 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2018
    The Turtle House is a very nice house to rent, conveniently located on Thomas Street, which is close to the wide variety of stores and restaurants on Duvall Street in downtown...
    Reviewed 23 June 2017
    Spacious property with two pools, friendly neighbors and charming location just a short walk to all of old town Key West.
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated historic house. The house can comfortably accommodate a maximum of six (6) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Tranquility1 / 24
    (31)Very good
    0.7 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed 29 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Key West Charming1 / 24
    (26)Very good
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 January 2016
    The location was awesome, close to everything. We loved that it was close to Blue Heaven. The condo was too small for our liking, but that's not to say that it isn't...
    Reviewed 2 December 2013
    this was a great condo and the location was perfect for the boat races. very clean and everything was just as stated.no problems at all!! and @home in key west were great...
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    About this property
    Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental! Located at the Shipyard Condominiums condo rental in Key West. This downstairs 2 bedroom 1...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Perfect Pineapple1 / 18
    (9)Very good
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 December 2019
    This was a very cozy little house in the perfect location! We and our guests were able to walk to our favorite places within minutes! We rented for 2 months. The pool was...
    Reviewed 6 March 2013
    Great location within walking distance to Duval and the Seaport. Even with two bedrooms it would be a bit crowded with more than three people . A few negatives are the laundry...
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    About this property
    Sit along side your private pool for morning coffee or your evening glass of wine. Long considered a sign of hospitality, the pineapple is now widely recognized as sign of Welcome and Friendship.....and so we welcome YOU to the Perfect Pineapple!br> On the corner of Southard and Margaret streets...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Amelia Home1 / 24
    (57)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2019
    We enjoyed every thing about this house. Close enough to Duval. The pool was perfect size for 4 people.
    Reviewed 5 February 2019
    Amelia House was a lovely place to stay. Very clean and an excellent location! The heated pool was perfect as it was a bit chilly when we stayed. We walked everywhere from here.
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    About this property
    After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home! The Amelia home is a 2 bedroom 2.5 bath retreat with sparkling private pool that is only four blocks from the Atlantic Ocean...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time? How about an evening stroll through the tropical jungle in your own backyard? Or maybe a scenic bike ride along the beach to experience the sunset? At Atlantic Paradise, all this can...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Key West Suites Hotel unit 2011 / 16
    (1)Excellent
    0.9 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2019
    Stayed at this apartment for New Year’s Eve, location is exceptional! Owners were available at all times for questions/concerns. The unit was very clean and equipped. It was...
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    About this property
    Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Emma's Secret1 / 22
    (1)Excellent
    0.8 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens. Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool. Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Key West Suites Hotel 2051 / 16
    (2)Very good
    0.9 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
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    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2020
    We did not sleep well in this unit. Was right next to a bar with super loud music. We complained to police and it got better for that night, but still bad. Every single night...
    Reviewed 21 March 2019
    I never normally write reviews for places, but this place was great! I stayed there for a few days with my friends and had never been to Key West before and this place had...
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    About this property
    Key West Suites Hotel 205 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Breezy Bungalow1 / 24
    (3)Very good
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2019
    Breezy Bungalow was a perfect place for the 4 of us. At Home in Key West were very accommodating and pleasant to work with. The Bungalow was clean, pool was perfect and the...
    Reviewed 12 November 2018
    The unit was pleasant enough but needs some attention. It was very badly lit and made it hard for all the occupants to be able to read etc at one time. There was no lighting on...
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    About this property
    Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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