Holiday Rentals with Pools in Key West
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213 rentals in Key West.
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
2 bedrooms
2 bathrooms
Sleeps 6
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
2 bedrooms
2 bathrooms
Sleeps 6
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Seaside Place Key West FL 5 Bedroom House 4 Baths
5 bedrooms
4 bathrooms
Sleeps 12
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6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
6 bedrooms
7 bathrooms
Sleeps 16
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Secret Villa I * Old Town with Private Pool, close to Duval!
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
3 bedrooms
2 bathrooms
Sleeps 8
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LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
1 bedroom
1 bathroom
Sleeps 4
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Island Hideaway
2 bedrooms
2 bathrooms
Sleeps 6
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
2 bedrooms
2 bathrooms
Sleeps 6
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Artist Cottage in Truman Annex
2 bedrooms
1 bathroom
Sleeps 4
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Sunrise At Seaside Condo 2 bedroom 2 bath
2 bedrooms
2 bathrooms
Sleeps 5
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval
3 bedrooms
3 bathrooms
Sleeps 8
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Casa Del Sol, a Key West Vacation (Truman Annex)
2 bedrooms
3 bathrooms
Sleeps 6
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Sunrise at Seaside Condo 2 Bedroom
2 bedrooms
2 bathrooms
Sleeps 5
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2 bedrooms
2 bathrooms
Sleeps 6
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Real World MTV House Key West
10 bedrooms
6 bathrooms
Sleeps 20
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Henry's Piece Of Paradise On The Ocean In Key West
2 bedrooms
2 bathrooms
Sleeps 5
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Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -
2 bedrooms
3 bathrooms
Sleeps 4
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
1 bedroom
1 bathroom
Sleeps 2
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2 bedrooms
1 bathroom
Sleeps 4
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Conch Get Enough! - Key West's Old Town Truman Annex
2 bedrooms
3 bathrooms
Sleeps 4
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Harbor Walk Hideaways
4 bedrooms
3 bathrooms
Sleeps 8
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Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
3 bedrooms
3 bathrooms
Sleeps 6
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
3 bedrooms
3 bathrooms
Sleeps 6
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
3 bedrooms
3 bathrooms
Sleeps 8
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Attitude Key West (2 Bikes and Wireless Internet)
2 bedrooms
1 bathroom
Sleeps 2
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Harbour Place 115 in Truman Annex Key West
2 bedrooms
3 bathrooms
Sleeps 6
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The Mermaids House, Historic Old Town Key West
2 bedrooms
1 bathroom
Sleeps 4
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Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.
2 bedrooms
3 bathrooms
Sleeps 6
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Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool
2 bedrooms
2 bathrooms
Sleeps 6
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
3 bedrooms
3 bathrooms
Sleeps 8
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Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo
3 bedrooms
3 bathrooms
Sleeps 8
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Conch Haven Old Town 1/1 MONTHLY Rental
1 bedroom
1 bathroom
Sleeps 4
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'SOUTHERNMOST BELLE'~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
5 bedrooms
4 bathrooms
Sleeps 10
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Tropical Key West Get Away
3 bedrooms
3 bathrooms
Sleeps 8
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'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!
2 bedrooms
3 bathrooms
Sleeps 6
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A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20
8 bedrooms
8 bathrooms
Sleeps 20
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Truman Annex Best Location in Town
2 bedrooms
1 bathroom
Sleeps 5
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI
2 bedrooms
1 bathroom
Sleeps 4
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BEST DEAL IN THE KEYS!
2 bedrooms
1 bathroom
Sleeps 6
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Craig & Cindy Key West Truman Annex 212 Fleming House
2 bedrooms
3 bathrooms
Sleeps 6
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Sunshine suit (2/2 apartment)
2 bedrooms
2 bathrooms
Sleeps 6
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Truman Annex, two blocks from Duval
2 bedrooms
3 bathrooms
Sleeps 4
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'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!
1 bedroom
1 bathroom
Sleeps 4
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Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families
2 bedrooms
2 bathrooms
Sleeps 4
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'THE QUARTERDECK' ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!
2 bedrooms
1 bathroom
Sleeps 4
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Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
2 bedrooms
3 bathrooms
Sleeps 6
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New Listing Family Friendly
3 bedrooms
3 bathrooms
Sleeps 6
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Spacious 3BR/3BA Catamaran as Private Sailing Charter up to 7 nights in Key West
3 bedrooms
3 bathrooms
Sleeps 6
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