Key West Vacation Rentals: Key West Rentals with Heated Pools

Compare 74 Key West vacation rentals and Airbnbs with heated pools and free parking. Check guest scores up to 98 and book the stay that fits your trip

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61-72 out of 72
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  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
5.0
Needs improvement1 total review
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899 yd from City Center904 yd from Smathers Beach
Heated PoolHot TubTennis Court
  • Steps from Smathers Beach
  • Private hot tub and spa
  • Heated pool with loungers
FromUS$ 1 622 /nightSelect
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194 yd from City Center1279 yd from Dog Beach
Heated PoolSpa CenterTennis Court
  • Four-bedroom holiday home with spa
  • Heated pool and spa facilities
  • Private tennis court on site
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1.2 mi from City Center568 yd from San Carlos Institute Casa Cuba
Heated PoolTennis CourtSpa Facilities
  • Entire property with private entrance
  • On-site tennis court
  • Heated pool and BBQ area
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1679 yd from City Center189 yd from Key West Butterfly and Nature Conservatory
Full KitchenBarbecueSofa Bed
  • Steps from Duval & South Beach
  • Full kitchen with barbecue
  • Pets allowed in studio
FromUS$ 461 /nightSelect
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739 yd from City Center917 yd from Key West Cemetery
Private PoolOutdoor DiningBeach Access
  • Three-bedroom holiday home
  • Private outdoor pool access
  • Fully equipped kitchen available
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1.1 mi from City Center589 yd from Key West Cemetery
Private PatioFull KitchenWasher Dryer
  • Private patio for outdoor dining
  • Full kitchen with cookware
  • In-unit washer and dryer
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1.0 mi from City Center413 yd from Key West Cemetery
Private PoolOutdoor PoolCity View
  • Nine-bedroom holiday home
  • Private pool and garden
  • Cycling and water sports
FromUS$ 1 415 /nightSelect
8 adults
4 bedrooms
4 beds
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854 yd from City Center1030 yd from Key West Cemetery
Heated PoolFull KitchenBBQ Grill
  • Spacious 4-bedroom holiday home
  • Heated outdoor pool
  • Fully equipped kitchen
FromUS$ 1 670 /nightSelect
Seafarer'S RefugeHoliday home
10 adults
4 bedrooms
4 beds
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914 yd from City Center1003 yd from Key West Cemetery
Private PoolHot TubMassage Services
  • Private pool with sea views
  • Spacious 4-bedroom holiday home
  • On-site massage and hot tub
FromUS$ 1 483 /nightSelect
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1.3 mi from City Center449 yd from San Carlos Institute Casa Cuba
Private PoolFree ParkingWater Sports
  • Seven-bedroom apartment with private pool
  • Free private parking on site
  • On-site water sports and fishing
FromUS$ 3 573 /nightSelect
8.5
Great8 total reviews
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1.3 mi from City Center378 yd from San Carlos Institute Casa Cuba
Outdoor PoolWater SportsGolf Course
  • Private cottage with full kitchen
  • Outdoor pool and garden
  • On-site water sports and golf
FromUS$ 519 /nightSelect
Salvador'S SeclusionHoliday home
6.2
Nice7 total reviews
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1.3 mi from City Center323 yd from Ernest Hemingway House
Massage ServicesTour DeskKitchenette
  • 3-minute walk to Fort Zachary State Park Beach
  • In-room massage services available
  • Steps from Hemingway Home and Museum
FromUS$ 258 /nightSelect

Key West vacation rentals offer travelers the freedom of a home away from home, with fully equipped kitchens, private outdoor pools, and free on-site parking. Most properties are located in the Old Town district, steps from Duval Street, South Beach, and the Southernmost Point. Budget for mid-range to upscale stays, with rates varying by season and size. Many rentals include free WiFi, air conditioning, and laundry facilities, making them ideal for families, groups, or extended trips.

Among the top-rated options, Coral Hammock Poolside Home earns a 98 guest score for its heated pool and massage services. KW42 Bahama House scores 90 and features a spa, restaurant, and a short walk to South Beach. Rose Lane Villas (86) offer villas adjacent to Duval Street with a heated pool and full kitchens. For airport convenience, Tortuga Suite at Sunrise Suites Resort includes a heated pool, hot tub, and free parking. These properties cater to visitors seeking privacy, space, and resort-style amenities without the hotel atmosphere.