Key West Luxury Holiday Homes
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
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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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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~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
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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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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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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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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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Living the Dream Key West Style
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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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Key West Home on Golf Course w/ Patio & Grill!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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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**THE SMILING IBIS * OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
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The Cozy Little Cottage!
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**FOLLOW THE SUN * THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY
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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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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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BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
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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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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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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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Villa La Isla- Luxury Vacation Rental 1/2 block from Duval
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SEA CONCH~ Amazing location with shared pool, deck, and parking!
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**SPIRIT OF KEY WEST * OLD TOWN** Exquisite Home & Pool + LAST KEY SERVICES…
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Spend your Holidays at Frogmore on Fleming in Downtown Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Village: 12BD/9BA Enclave for Large Groups. Gated. Pool/Hot
Holiday Rental House
12 bedrooms
9 bathrooms
Sleeps 30
Match: Sleeps
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Beautiful Key West! Close to the Beach! Amazing Ocean View, Outdoor Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Jasmine House Just a 2 minute walk to Duval and restaurants and bars
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Fantastic Land and Sea Vacation! Two Convenient Rooms, Outdoor Pool!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secret Courtyard cottage steps from Duval
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SUN, SEA, AND SKY at The Truman Annex in Key West
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Lightkeepers Quarters | 5 bed/5 bath residence with pool
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Charming 4-bedroom house with pool & spa- 10 MIN. WALK TO DUVAL STREET
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rooster Doodle Do - Midtown Family Retreat
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Escape to the wonderful Cuban Paradise!
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Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Waterfront Home - Haven House
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Condo with Old Florida Charm, Wrap-Around Balcony & Large Pool!
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LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
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Dee's Dream Sunset Condo with WiFi and AC in Key West - 2 bdrm - Shipyard #151
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Ocean Front Presidential Suite | Beachside Resort
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Land and Sea Getaway! Four Convenient Rooms, Close to Nearest Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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FANTASY FEST WEEK 2023
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cat Island Suite | Beautifully Renovated w/ Pool!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mermaid's Retreat at Coral Hammock Key West Island living at its best
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming 1-bedroom/1-bath apartment in historical home with pool in Key West
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sea Breeze Suite 101 - Dog-friendly, pool, reserved parking!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rent at PORCHSIDE PARADISE - Steps to Duval
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Comfortable Condo with Pool, Private Balcony, & Beach Access
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Sunset Suite-2 BR, sleeps 4, King and Queen, Spa!
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