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Key West
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Key West Holiday Rentals with Pools
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Kid friendly (83)
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Condominium/Apartment (59)
Holiday Rental House (28)
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Cabin Holiday Rental (0)
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5 km
Key West Butterfly and Nature Conservatory
The Ernest Hemingway Home and Museum
Yankee Freedom Dry Tortugas Ferry
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88 rentals
in Key West.
Island Suite @ KW Vacation
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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One-bedroom time share suite in the heart of Old Key West
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Sunshine suit (2/2 apartment)
2 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, All pools
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A Change in Latitudes - TRUMAN ANNEX
1 review
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
101 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Private, heated pool. Private yard.
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, All pools
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Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps, All pools
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Comfy Family Home in a Gorgeous Gated Community
4 reviews
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, All pools
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Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Lovely 2 bedroom, 2 bath condo at La Brisa.
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, All pools
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White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, All pools
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Sunrise at Seaside Condo 2 Bedroom
41 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps, All pools
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Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach
1 review
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Key West Gulf front Home with private dock and pool.
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, All pools
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Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, All pools
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NEW LISTING! 40’ Luxury Catamaran Yacht!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps, All pools
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Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Key West Bayfront Paradise - House and Private Pool! Steps from shops and food
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, All pools
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Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
13 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Artist Cottage
13 reviews
Condo/Apartment
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Henry's Piece Of Paradise On The Ocean In Key West
38 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps, All pools
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Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beach
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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HISTORIC KEY WEST - Cigar House - Sleeps 4
2 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Casa Del Sol, a Key West Vacation (Truman Annex)
113 reviews
Holiday Rental House
View on map
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean
17 reviews
Condo/Apartment
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes
5 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, All pools
More info
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HISTORIC KEY WEST - Conch House - Sleeps 5
6 reviews
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps, All pools
More info
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI
17 reviews
Condo/Apartment
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Paradise: Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk T
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Seaside Condo 2 pools. sunny, quiet, near Old Town
2 reviews
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps, All pools
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HISTORIC KEY WEST - Turtle House - Sleeps 6
3 reviews
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, All pools
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Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
1 review
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, All pools
More info
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
17 reviews
Condo/Apartment
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West
Condo/Apartment
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3 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps, All pools
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
44 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Tranquility by Smathers and 10 minute bike downtown Key West value savings
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Key West Affordable Ocean View Condo. Clean priced well on the Atlantic
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Top floor, two bedroom,two bath condo with private balcony,close to the Ocean
4 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.
67 reviews
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
1 review
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
1 review
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
2 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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