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263 rentals
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
94 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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ATLANTIC PARADISE Condo 1800 Atlantic, shared pool, jacuzi, BBQ, family fun!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
17 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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KEY WEST CASA Large Condo, Truman Annex, Shared Pool, Downtown Key West
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Casa Del Sol, a Key West Vacation (Truman Annex)
103 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Clean Apartment in Old Town Key West (Best Downtown Locations)
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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AMELIA HOME Spacious Private Home with Private Pool, BBQ Grill + Pet Friendly
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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The Tree House Old Town 2 Bedroom MONTHLY Rental
7 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
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Conch Haven Old Town 1/1 MONTHLY Rental
6 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Artist Cottage in Truman Annex
13 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Harbor Walk Hideaways
22 reviews
Private Room
4 bedrooms
3 bathrooms
Sleeps 8
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Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8
11,796 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
218 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
68 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
126 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
80 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool
129 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S
89 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Attitude Key West (2 Bikes and Wireless Internet)
142 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Secret Villa I * Old Town with Private Pool, close to Duval!
87 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
98 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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My Condo by the Beach with Ocean View
118 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Sea Breeze Cottage- in Beautiful Truman Annex
127 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Tom's 2000sf Direct Oceanfront Penthouse. Renovated, Heated Pool, Close To Beach
78 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Seaside Place Key West FL 5 Bedroom House 4 Baths
42 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna
196 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Catherine House: A charming Old Town Key West cottage
158 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
115 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Boli Townhouse - Luxury Rental in gated Truman Annex
130 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Harbour Place 115 in Truman Annex Key West
66 reviews
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis
223 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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William Skelton House - Available Easter Weekend!
132 reviews
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
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The Mermaids House, Historic Old Town Key West
36 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
44 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi
93 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
85 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Apple of Your Eye in Paradise (Truman Annex)!
77 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Villa Paradiso: A unique mid-town paradise
142 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
71 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
162 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Enjoy More Privacy in a Truman Annex End Unit Townhome
117 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Duval Square Penthouse: A large, beautiful condo steps from the action
102 reviews
Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 10
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval
141 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Ann Street Cottage: A bright and airy home near Duval Street
137 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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Beach House with Ocean View-No Contact Check-In
102 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.
78 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
60 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
91 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!
92 reviews
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Peaceful Setting Amongst The Active Island Life Style
69 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Frequently Asked Questions about Key West
Do any holiday rentals in Key West have a pool?
Yes, here are some popular holiday rentals in Key West that have a pool:\n
\n
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
\n
HISTORIC KEY WEST - Main House - Sleeps 8
\n
HISTORIC KEY WEST - Turtle House - Sleeps 6
\n
\n
See all holiday rentals with a pool in Key West on Tripadvisor
Do any holiday rentals in Key West have internet access?
Yes, here are some popular holiday rentals in Key West that have internet access:\n
\n
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
\n
HISTORIC KEY WEST - Main House - Sleeps 8
\n
HISTORIC KEY WEST - Turtle House - Sleeps 6
\n
\n
See all holiday rentals in Key West on Tripadvisor
What are the best pet friendly rentals in Key West?
The best pet friendly rentals in Key West are:\n
\n
Ocean View Estate with Private Pool 15 minutes from Key West
\n
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
\n
The Tree House Old Town 2 Bedroom MONTHLY Rental
\n
\n
See all pet friendly holiday rentals in Key West on Tripadvisor
What are some great rentals in Key West that are kid friendly?
Some of the most popular kid friendly rentals in Key West are:\n
\n
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
\n
HISTORIC KEY WEST - Main House - Sleeps 8
\n
HISTORIC KEY WEST - Turtle House - Sleeps 6
\n
\n
See all kid friendly holiday rentals in Key West on Tripadvisor