Holiday Rentals with Pools in Key West
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170 rentals in Key West.
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6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Casa Del Sol, a Key West Vacation (Truman Annex)
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Artist Cottage in Truman Annex
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Attitude Key West (2 Bikes and Wireless Internet)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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My Condo by the Beach with Ocean View
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Sea Breeze Cottage- in Beautiful Truman Annex
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Secret Villa I * Old Town with Private Pool, close to Duval!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Seaside Place Key West FL 5 Bedroom House 4 Baths
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Catherine House: A charming Old Town Key West cottage
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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William Skelton House - Available Easter Weekend!
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Boli Townhouse - Luxury Rental in gated Truman Annex
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Harbour Place 115 in Truman Annex Key West
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Enjoy More Privacy in a Truman Annex End Unit Townhome
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Duval Square Penthouse: A large, beautiful condo steps from the action
Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Villa Paradiso: A unique mid-town paradise
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Apple of Your Eye in Paradise (Truman Annex)!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Ann Street Cottage: A bright and airy home near Duval Street
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, All pools
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NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beach House with Ocean View-No Contact Check-In
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Peaceful Setting Amongst The Active Island Life Style
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Duval Square Retreat: A beautiful condo steps from the action
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Conch Retreat in Beautiful Truman Annex with 2 Bikes
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Louisa House: A comfortable four bedroom vacation hideaway
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Henry's Piece Of Paradise On The Ocean In Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Colony Poolside: A charming bungalow near the historic cemetery
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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