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      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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      Rooms and Guests2 Guests, 1 room
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      Rooms and Guests2 Guests, 1 room
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      Hotels
      Vacation rentals
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      Holiday homes (55)Apartments (17)
      21-40 out of 72
      Sort by: high popularity
      • Price: low to high
      • Price: high to low
      • Guest rating: high to low
      • Popularity: high to low
      Kw353B Seagrass SuiteApartment
      9.2
      Perfect14 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center156 yd from Ernest Hemingway House
      Full KitchenPlaygroundGolf Course
      • Fully equipped kitchen in suite
      • Children's playground on-site
      • On-site golf course available
      FromUS$ 289 /nightSelect
      Casa Key West-Pool & Free ParkingHoliday home
      7.1
      Very good17 total reviews
      our site & Booking.com
      8 adults
      3 bedrooms
      4 beds
      Map
      1.0 mi from City Center278 yd from Ernest Hemingway House
      Outdoor PoolPrivate ParkingFull Kitchen
      • Three-bedroom home with private entrance
      • City-view patio from each bedroom
      • Free private parking on premises
      FromUS$ 1 170 /nightSelect
      Duval Street Suite W Parking And PoolApartment
      9.1
      Perfect14 total reviews
      our site & Booking.com
      Map
      1.1 mi from City Center123 yd from Ernest Hemingway House
      Private PoolFree ParkingFull Kitchen
      • Private pool in apartment
      • Free private parking on-site
      • Steps from Duval Street
      FromUS$ 636 /nightSelect
      Kw44 Conch CasaHoliday home
      9.3
      Perfect10 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.1 mi from City Center194 yd from Ernest Hemingway House
      JacuzziFull KitchenWasher/Dryer
      • Private in-home jacuzzi
      • Full kitchen for cooking
      • Steps from Duval Street
      FromUS$ 614 /nightSelect
      St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock PetHoliday home
      9.2
      Perfect10 total reviews
      our site & Booking.com
      Map
      705 yd from City Center1033 yd from Key West Cemetery
      Waterfront ViewPrivate PoolWater Sports
      • Private waterfront penthouse with sea views
      • On-site water sports facilities
      • Private outdoor pool and dock
      FromUS$ 2 229 /nightSelect
      Kwss311 Sunrise Suites Catalina Suite #311Apartment
      8.8
      Great23 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center1199 yd from Kayak Kings Key West
      Heated PoolTennis CourtHot Tub
      • Heated outdoor swimming pool
      • On-site tennis court
      • Pet-friendly two-bedroom suites
      FromUS$ 569 /nightSelect
      Papaya Place By AvantstayHoliday home
      8.7
      Great12 total reviews
      our site & Booking.com
      Map
      796 yd from City Center990 yd from Smathers Beach
      Hot tubOutdoor poolFitness center
      • Beachside holiday home with pool
      • Private hot tub on balcony
      • Sea views from every bedroom
      FromUS$ 556 /nightSelect
      Kw24 Key Lime CalypsoHoliday home
      8.2
      Great12 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.2 mi from City Center150 yd from Fury Water Adventures Key West
      Heated PoolOutdoor PoolKitchenware
      • Heated outdoor pool on-site
      • Steps from Duval Street
      • Non-smoking holiday home
      FromUS$ 333 /nightSelect
      Sky Suite On DuvalApartment
      9.2
      Perfect9 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center86 yd from Fury Water Adventures Key West
      Water ParkGolf CoursePrivate Patio
      • Two-bedroom suite with 3 baths
      • On-site water park for guests
      • Private patio with city views
      FromUS$ 648 /nightSelect
      Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-FriendlyHoliday home
      9.6
      Perfect17 total reviews
      our site & Booking.com
      Map
      705 yd from City Center1033 yd from Key West Cemetery
      Private DockOutdoor PoolLift Access
      • Private waterfront dock with pool
      • Pet-friendly with private entrance
      • Sea-view patio with dishwasher
      FromUS$ 1 038 /nightSelect
      Just Steps To Duval- Sleeps 10- Heated Pool HouseHoliday home
      8.0
      Great10 total reviews
      our site & Booking.com
      Map
      1.1 mi from City Center83 yd from Ernest Hemingway House
      Heated PoolFull KitchenGarden
      • Heated pool for year-round swims
      • Steps from Duval Street nightlife
      • Historic 1928-built vacation home
      FromUS$ 1 183 /nightSelect
      Kw353C Mermaid'S RetreatApartment
      8.0
      Great8 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center156 yd from Ernest Hemingway House
      Golf CourseChildren's PlaygroundFull Kitchen
      • On-site golf course
      • Children's playground on-site
      • Full kitchen in apartment
      FromUS$ 365 /nightSelect
      Coral Hammock Poolside HomeHoliday home
      9.8
      Perfect6 total reviews
      our site & Booking.com
      Map
      3.1 mi from City Center1228 yd from Kayak Kings Key West
      Heated PoolPrivate ParkingTennis Court
      • Heated private pool
      • Private on-site parking
      • Fully equipped kitchen
      FromUS$ 511 /nightSelect
      Casita De Catherine By AvantstayHoliday home
      9.2
      Perfect7 total reviews
      our site & Booking.com
      Map
      1.1 mi from City Center156 yd from Duval Street
      Hot TubBeach AccessFull Kitchen
      • Private hot tub on patio
      • Short walk to South Beach
      • Full private kitchen
      FromUS$ 446 /nightSelect
      Yellowfin LedgeHoliday home
      10.0
      Perfect4 total reviews
      our site & Booking.com
      Map
      1.1 mi from City Center125 yd from Duval Street
      KitchenetteSofa Bed
      • 3-min walk to South Beach
      • Holiday home with kitchenette
      • Pets allowed on site
      FromUS$ 236 /nightSelect
      Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval!Holiday home
      7.8
      Very good6 total reviews
      our site & Booking.com
      Map
      1679 yd from City Center189 yd from Key West Butterfly and Nature Conservatory
      Hot TubsWater SportsBBQ Grill
      • Steps from South Beach & Duval
      • Private hot tubs available
      • Fully equipped kitchen
      FromUS$ 766 /nightSelect
      Jasmine PlaceHoliday home
      9.7
      Perfect3 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center42 yd from Ernest Hemingway House
      Private PoolFitness CenterBBQ Area
      • Private pool and barbecue
      • City center near Duval Street
      • Pet-friendly holiday home
      Select
      Darling Of Duval By Last Key RealtyHoliday home
      8.0
      Great2 total reviews
      our site & Booking.com
      Map
      1.4 mi from City Center367 yd from San Carlos Institute Casa Cuba
      Hot TubSpa CenterTennis Court
      • Holiday home with two bedrooms
      • Spa facilities and hot tub
      • Steps from Duval Street
      FromUS$ 1 598 /nightSelect
      The Crestwood House - Private Heated Pool & ParkingHoliday home
      10.0
      Perfect1 total review
      our site & Booking.com
      Map
      3.3 mi from City Center1.0 mi from Kayak Kings Key West
      Heated PoolFitness CenterPrivate Parking
      • Private heated pool
      • Six-bedroom holiday home
      • On-site fitness center
      FromUS$ 2 726 /nightSelect
      The Mesa House-Close To Duval!Holiday home
      7.0
      Very good2 total reviews
      our site & Booking.com
      10 adults
      3 bedrooms
      5 beds
      Map
      1.3 mi from City Center461 yd from Mallory Square
      Full KitchenPrivate PatioCity Views
      • Whole-home private rental
      • Fully equipped kitchen
      • Patio with city views
      FromUS$ 1 393 /nightSelect
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      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.