Holiday Rentals in Key West
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Bedrooms
Bathrooms
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Property type
Distinctive Features
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854 rentals in Key West.
Pool, Laundry, and grilling area
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Southern Skies, Stylish Home in Old Town Key West
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Fisherman's Paradise on deep water canal, boat dock, ocean access
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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**HOUSE OF THE ROYAL PALMS * OLD TOWN** Estate & Pool Near Duval + LAST KEY SERV
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
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Amazing Stay in the Keywest! Two Deluxe Pool View Two Queen Beds
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Andros | Incredible Views w/ Shared Pool
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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**FOLLOW THE SUN * THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY
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The Cozy Little Cottage!
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**THE SMILING IBIS * OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
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Atlantis House's Palm Suite-voted top 25 in USA
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Key West Home on Golf Course w/ Patio & Grill!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated Hotel w/ Outdoor Pool | Short Drive to Historic Old Town
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Living the Dream Key West Style
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L'Attitude Adjustment | 3 Bed, 2 Bath with pool in Key West
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W/D
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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ISLAND DREAMIN' ~ Exceptional 4 BR/3.5 Ba Home w/ Pool!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
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POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Beach House Condo by AvantStay | Communal Pool, Gated Community | Great Location
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Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality at its Best.
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SEAPORT SKYLINE at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
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Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
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Conch Cove - 3br/3ba with private heated pool and private parking
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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My Condo by the Beach with Ocean View
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Orchids in Paradise Near White Pier
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
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Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 2, Swimming Pool, Hot Tub
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Touch Of Cuba In Key West
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Tropical Village: Toon Hall - Quiet & gated. Spacious! Pool/Decks/Pet friendly
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Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
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~AZUR PALM~ Oceanfront elegance with pools, peace, and a designer interior!
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Key West Oasis 2 blocks from White Street Pier
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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~BLUE HAVEN~ Welcome to this single-story retreat with a pool!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Grinnell Getaway: Elegant 3BR Oasis in Old Town Key West, Shared Pool, Near
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval
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Key West, Hyatt Condo, 4 nights ONLY, Sun, 3/16 out Thurs, 3/20/25
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Leonella, Old Town Key West.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Best Place to Stay in Key West! 4 Stylish Units, Pool! Parking & EV Charger
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Lovely 2 bedroom, 2 bathroom steps from the beach!
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4x Pool View Two Queen Beds at The Gates Hotel Key West, Onsite Swimming Pool!
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Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800
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Key West Retreat Near Duval Street | Scenic Resort w/ Outdoor Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Coconut Cottage Sunset Marina-2bed 2bath oceanfront condo w/pool, dock space
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 854
Frequently Asked Questions about Key West
- Yes, here are some popular holiday rentals in Key West that have a pool:
- Pool, Laundry, and grilling area
- Southern Skies, Stylish Home in Old Town Key West
- Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
- Yes, here are some popular holiday rentals in Key West that have internet access:
- Pool, Laundry, and grilling area
- Southern Skies, Stylish Home in Old Town Key West
- Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
- Some of the most popular kid friendly rentals in Key West are:
- Southern Skies, Stylish Home in Old Town Key West
- Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
- Key West vibes, 2-bedroom townhome with AC, WiFi in marvelous Key West
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