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Key West Vacation Homes and Villas with Pools

Find Luxury Places to Stay Near Key West with a Swimming Pool. Find pool in Key West, Florida.

Pool

Only stays with pool access are shown on this page

85 stays

a living room with yellow walls and a ceiling fan at Rose Lane Villas in Key West

From US $319

Rose Lane Villas Pool available

8.5 (306 Reviews) Villa

Houses • Private parking • Outdoor swimming pool

Key West The Hemingway Home and Museum • 805m from The Hemingway Home and Museum

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a large blue swimming pool with palm trees in the background at Grand Marina Suite -Waterfront Condo in Key West

From US $519

Grand Marina Suite -Waterfront Condo Pool available

8.6 (138 Reviews) Holiday_home

The entire place is yours • 165 m² size • Free on-site parking

Key West Key West International Airport • 3.1km from Key West International Airport

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a living room with a blue couch and a kitchen at Tortuga Suite at Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking in Key West

From US $459

Tortuga Suite at Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking Pool available

8.4 (55 Reviews) Holiday_home

The entire place is yours • 74 m² size • Free on-site parking

Key West Key West International Airport • 749m from Key West International Airport

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a bedroom with a large bed with a wooden headboard at The Island Suite at KW Vacation in Key West

From US $307

The Island Suite at KW Vacation Pool available

9.2 (37 Reviews) Apartment

The entire place is yours • 46 m² size • Free parking

Key West The Hemingway Home and Museum • 878m from The Hemingway Home and Museum

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a house with a green door and palm trees at Heron Hideaway in Key West

From US $407

Heron Hideaway Pool available

9.5 (11 Reviews) Apartment

The entire place is yours • 58 m² size • Free parking

Key West The Hemingway Home and Museum • 1.1km from The Hemingway Home and Museum

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a swimming pool with palm trees in the background at The Trinidad -Pool & Parking in Key West

From US $428

The Trinidad -Pool & Parking Pool available

8.1 (31 Reviews) Holiday_home

The entire place is yours • 74 m² size • Free on-site parking

Key West Key West International Airport • 748m from Key West International Airport

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a dining room and living room with a table and chairs at Sky Loft in Key West in Key West

From US $590

Sky Loft in Key West Pool available

9.3 (23 Reviews) Holiday_home

The entire place is yours • 63 m² size • Outdoor swimming pool

Key West The Hemingway Home and Museum • 549m from The Hemingway Home and Museum

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a swimming pool in front of a house at Amelia Home by AvantStay In Historic Old Town w Pool in Key West

From US $866

Amelia Home by AvantStay In Historic Old Town w Pool Pool available

9.4 (10 Reviews) Holiday_home

The entire place is yours • 127 m² size • Kitchen

Key West The Key West Butterfly and Nature Conservatory • 361m from The Key West Butterfly and Nature Conservatory

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a house with a white fence in front of it at Key West Villas in Key West

From US $349

Key West Villas Pool available

9.6 (309 Reviews) Villa

Houses • Breakfast • Private parking

Key West The Hemingway Home and Museum • 322m from The Hemingway Home and Museum

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a bedroom with a bed with blue and green wallpaper at Duval Street Suite with pool in Key West

From US $329

Duval Street Suite with pool Pool available

9.8 (8 Reviews) Apartment

The entire place is yours • 37 m² size • Outdoor swimming pool

Key West The Hemingway Home and Museum • 110m from The Hemingway Home and Museum

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a large swimming pool with the ocean in the background at Atlantic Paradise by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub in Key West

From US $693

Atlantic Paradise by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub Pool available

8.6 (13 Reviews) Holiday_home

The entire place is yours • 122 m² size • Kitchen

Key West The Key West Butterfly and Nature Conservatory • 2.0km from The Key West Butterfly and Nature Conservatory

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a swimming pool with blue chairs and a swimming pool at New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool in Key West

From US $687

New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool Pool available

8.1 (16 Reviews) Holiday_home

The entire place is yours • 116 m² size • Kitchen

Key West The Hemingway Home and Museum • 268m from The Hemingway Home and Museum

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a swimming pool with two chairs and a table at Keys Please! in Key West

From US $1200

Keys Please! Pool available

9.4 (9 Reviews) Holiday_home

The entire place is yours • 114 m² size • Free parking

Key West The Key West Butterfly and Nature Conservatory • 163m from The Key West Butterfly and Nature Conservatory

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a living room with a blue couch and a table at Casa Key West-Pool & Free Parking in Key West

From US $1200

Casa Key West-Pool & Free Parking Pool available

8.2 (15 Reviews) Holiday_home

The entire place is yours • 139 m² size • Free on-site parking

Key West The Hemingway Home and Museum • 260m from The Hemingway Home and Museum

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a swimming pool in front of a house at Poolside Suite in Key West

From US $511

Poolside Suite Pool available

10.0 (3 Reviews) Apartment

The entire place is yours • 60 m² size • Free on-site parking

Key West The Hemingway Home and Museum • 183m from The Hemingway Home and Museum

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a pool with chairs and palm trees and the ocean at Beachfront 2BDR Condo Pool Hot Tub w Ocean Views Papaya Place by AvantStay in Key West

From US $596

Beachfront 2BDR Condo Pool Hot Tub w Ocean Views Papaya Place by AvantStay Pool available

8.4 (11 Reviews) Holiday_home

The entire place is yours • 122 m² size • Kitchen

Key West The Key West Butterfly and Nature Conservatory • 2.0km from The Key West Butterfly and Nature Conservatory

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a patio with a table and chairs on a balcony at Duval Breeze by AvantStay Great Location Close to Beach Nightlife Shared Pool Week Long Stays in Key West

From US $1000

Duval Breeze by AvantStay Great Location Close to Beach Nightlife Shared Pool Week Long Stays Pool available

9.0 (3 Reviews) Holiday_home

The entire place is yours • 113 m² size • Free on-site parking

Key West The Hemingway Home and Museum • 268m from The Hemingway Home and Museum

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a house with a swimming pool and palm trees at Paradise Place by AvantStay Key West Old Town Condo w Shared Pool in Key West

From US $453

Paradise Place by AvantStay Key West Old Town Condo w Shared Pool Pool available

7.0 (9 Reviews) Holiday_home

The entire place is yours • 42 m² size • Kitchen

Key West The Hemingway Home and Museum • 1.1km from The Hemingway Home and Museum

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a swimming pool with chairs and a house at Duval Sea Turtle by AvantStay Great Location Close to Shops Shared Pool in Key West

From US $956

Duval Sea Turtle by AvantStay Great Location Close to Shops Shared Pool Pool available

9.7 (3 Reviews) Holiday_home

The entire place is yours • 113 m² size • Kitchen

Key West The Hemingway Home and Museum • 268m from The Hemingway Home and Museum

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a bedroom with a large white bed with two lamps at Sweet Caroline in Key West

From US $617

Sweet Caroline Pool available

7.6 (8 Reviews) Holiday_home

The entire place is yours • 118 m² size • Free on-site parking

Key West The Hemingway Home and Museum • 908m from The Hemingway Home and Museum

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a house with a swimming pool in front of a house at Tropical Dreaming by AvantStay 4 BLKS to Beach Private Pool in Key West

From US $1000

Tropical Dreaming by AvantStay 4 BLKS to Beach Private Pool Pool available

9.0 (3 Reviews) Holiday_home

The entire place is yours • 121 m² size • Kitchen

Key West The Key West Butterfly and Nature Conservatory • 361m from The Key West Butterfly and Nature Conservatory

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a patio with a table and chairs on a balcony at NEW Grenada Suite - Parking Pool & Pets 209 in Key West

From US $448

NEW Grenada Suite - Parking Pool & Pets 209 Pool available

7.0 (7 Reviews) Holiday_home

The entire place is yours • 74 m² size • Free on-site parking

Key West Key West International Airport • 746m from Key West International Airport

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a living room with a couch and a tv at Brisa Del Mar by AvantStay Communal Pool Gated Community Ocean Front in Key West

From US $637

Brisa Del Mar by AvantStay Communal Pool Gated Community Ocean Front Pool available

8.0 (4 Reviews) Holiday_home

The entire place is yours • 110 m² size • Kitchen

Key West Key West International Airport • 2.1km from Key West International Airport

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a swimming pool at a resort with a building in the background at Coral Villa by AvantStay Close 2 DT Key West Shared Pool Patio in Stock Island

From US $775

Coral Villa by AvantStay Close 2 DT Key West Shared Pool Patio Pool available

7.3 (3 Reviews) Villa

The entire place is yours • 129 m² size • Kitchen

Key West Key West International Airport • 2.7km from Key West International Airport

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a kitchen and dining room with a table and chairs at La Brisa Unit 105 North Building in Key West

From US $571

La Brisa Unit 105 North Building Pool available

6.7 (4 Reviews) Holiday_home

The entire place is yours • 79 m² size • Free on-site parking

Key West Key West International Airport • 2.1km from Key West International Airport

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a living room with a couch and a table at Atlantic Ocean View in Key West

From US $448

Atlantic Ocean View Pool available

8.6 (56 Reviews) Apartment

The entire place is yours • 126 m² size • Outdoor swimming pool

Key West The Key West Butterfly and Nature Conservatory • 2.0km from The Key West Butterfly and Nature Conservatory

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a swimming pool in the backyard of a house at Colors on White in Key West

From US $229

Colors on White Pool available

7.3 (88 Reviews) Apartment

Apartments • Free parking • Outdoor swimming pool

Key West The Hemingway Home and Museum • 1.1km from The Hemingway Home and Museum

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a living room with a couch and a tv at Sunrise Suites Cozumel Suite #112 in Key West

From US $286

Sunrise Suites Cozumel Suite #112 Pool available

7.8 (53 Reviews) Apartment

The entire place is yours • 72 m² size • Outdoor swimming pool

Key West Key West International Airport • 766m from Key West International Airport

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a pool in front of a resort with palm trees at Sunrise Suites Barbados Suite #204 in Key West

From US $520

Sunrise Suites Barbados Suite #204 Pool available

7.9 (42 Reviews) Apartment

The entire place is yours • 72 m² size • Kitchen

Key West Key West International Airport • 722m from Key West International Airport

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a pool at a resort with palm trees in the background at Sunrise Suites Panama Suite #310 in Key West

From US $453

Sunrise Suites Panama Suite #310 Pool available

7.8 (38 Reviews) Apartment

The entire place is yours • 72 m² size • Outdoor swimming pool

Key West Key West International Airport • 752m from Key West International Airport

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a house with a red door and a patio at Old Town Garden Villas - Andros Suite in Key West

From US $321

Old Town Garden Villas - Andros Suite Pool available

9.6 (18 Reviews) Apartment

The entire place is yours • 68 m² size • Outdoor swimming pool

Key West The Hemingway Home and Museum • 197m from The Hemingway Home and Museum

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a large swimming pool with palm trees in the background at Sunrise Suites Big Kahuna Suite #202 in Key West

From US $506

Sunrise Suites Big Kahuna Suite #202 Pool available

9.1 (21 Reviews) Apartment

The entire place is yours • 72 m² size • Outdoor swimming pool

Key West Key West International Airport • 714m from Key West International Airport

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a balcony with a pool and chairs and a straw umbrella at Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly in Key West

From US $697

Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly Pool available

9.8 (15 Reviews) Holiday_home

The entire place is yours • 111 m² size • Kitchen

Key West The Key West Butterfly and Nature Conservatory • 1.5km from The Key West Butterfly and Nature Conservatory

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a living room with a couch and a table at Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo in Key West

From US $462

Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo Pool available

9.1 (18 Reviews) Holiday_home

The entire place is yours • 121 m² size • Kitchen

Key West The Key West Butterfly and Nature Conservatory • 1.5km from The Key West Butterfly and Nature Conservatory

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a patio with a table and chairs on a balcony at Sunrise Suites Catalina Suite #311 in Key West

From US $431

Sunrise Suites Catalina Suite #311 Pool available

8.4 (22 Reviews) Apartment

The entire place is yours • 72 m² size • Outdoor swimming pool

Key West Key West International Airport • 749m from Key West International Airport

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a balcony with a table and chairs and a pool at Sunrise Suites Tierra Bomba Suite #403 in Key West

From US $336

Sunrise Suites Tierra Bomba Suite #403 Pool available

8.5 (21 Reviews) Apartment

The entire place is yours • 74 m² size • Outdoor swimming pool

Key West Key West International Airport • 752m from Key West International Airport

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About Key West Vacation Rentals with Pools on NearbyHoliday

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Find Key West Rentals, Hotels, and Resorts with Swimming Pools.

Discover 85 places to stay, including hotel waterparks, vacation homes, resorts, private villas, and condos in Key West that feature indoor, outdoor, or private pools.

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Vacation Rentals with Pools: Explore Top Destinations

Stay Near Key West's Top Attractions

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Frequently Asked Questions About Vacation Rentals With Pools in Key West

There are a lot of vacation rentals with pools in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals with Pools in Key West: