• My bookings1
  • Currency
    USD
    • CurrencyUSD (U.S. dollar)
      Popular currencies
        All currencies
          No currencies found
          Try changing your search

      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

      Check-in
      Fri, 09 Oct
      Check-out
      Sat, 10 Oct
      Rooms and Guests2 Guests, 1 room
      We’ll open Booking.com in a new tab for fair comparison.
      Check-in
      Fri, 09 Oct
      -
      Check-out
      Sat, 10 Oct
      Rooms and Guests2 Guests, 1 room
      1Filter & Sort
      View map
      Check-in
      Fri, 09 Oct
      -
      Check-out
      Sat, 10 Oct
      Rooms and Guests2 Guests, 1 room
      1Filter & Sort
      View map
      View map
      Hotels
      Vacation rentals
      All types
      Holiday homes (56)Apartments (18)
      1-20 out of 74
      Sort by: high popularity
      • Price: low to high
      • Price: high to low
      • Guest rating: high to low
      • Popularity: high to low
      Rose Lane VillasVilla
      8.6
      Great282 total reviews
      our site & Booking.com
      6 adults
      3 bedrooms
      3 beds
      Map
      1.3 mi from City Center334 yd from San Carlos Institute Casa Cuba
      Heated PoolFull KitchenPet Friendly
      • Fully equipped kitchen in each villa
      • Adjacent to Duval Street dining
      • Pet-friendly villas
      FromUS$ 709 /nightSelect
      Key West VillasVilla
      9.7
      Perfect293 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.1 mi from City Center72 yd from Fury Water Adventures Key West
      Heated PoolOutdoor SpaBike Rentals
      • Steps from historic Duval Street
      • Heated pool open year-round
      • In-room kitchen in apartments
      FromUS$ 314 /nightSelect
      Grand Marina Suite -Waterfront CondoHoliday home
      8.6
      Great127 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      3.7 mi from City Center943 yd from Safe Harbor
      Outdoor PoolFitness CenterWater Sports
      • Waterfront condo with private patio
      • On-site fitness and outdoor pool
      • Cycling and water sports available
      FromUS$ 325 /nightSelect
      Colors On WhiteApartment
      7.4
      Very good104 total reviews
      our site & Booking.com
      The largest option:
      4 adults
      1 bedroom
      2 beds
      Map
      1081 yd from City Center551 yd from Key West Cemetery
      Outdoor PoolBBQ AreaBicycle Hire
      • Colorful individually decorated rooms
      • Outdoor pool with waterfall
      • Kitchenette with cookware provided
      FromUS$ 245 /nightSelect
      Kw23 Atlantic Ocean ViewApartment
      8.7
      Great52 total reviews
      our site & Booking.com
      The largest option:
      6 adults
      2 bedrooms
      4 beds
      Map
      776 yd from City Center998 yd from Smathers Beach
      Outdoor PoolFull KitchenPrivate Balcony
      • Ocean-view private balcony
      • Fully equipped kitchen
      • Near Smathers Beach
      FromUS$ 408 /nightSelect
      Kwss112 Sunrise Suites Cozumel Suite #112Apartment
      7.7
      Very good64 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center1184 yd from Kayak Kings Key West
      Heated PoolHot TubTennis Court
      • Private hot tub and balcony
      • On-site restaurant and picnic area
      • Fully equipped kitchen in suite
      FromUS$ 374 /nightSelect
      Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free ParkingHoliday home
      8.5
      Great60 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center1201 yd from Kayak Kings Key West
      Heated PoolHot TubFree Parking
      • Heated pool and hot tub
      • Free parking included
      • Pet-friendly suite
      FromUS$ 379 /nightSelect
      Mesa House, Uno-Perfect LocationApartment
      7.0
      Very good44 total reviews
      our site & Booking.com
      4 adults
      1 bedroom
      2 beds
      Map
      1.3 mi from City Center461 yd from Mallory Square
      Full KitchenPrivate EntrancePatio
      • Private patio with city views
      • Full kitchen with dishwasher and oven
      • Private entrance for extra privacy
      FromUS$ 311 /nightSelect
      Sailors Cabin - Prime Downtown Key West Spot - Walk To DuvalApartment
      9.0
      Perfect36 total reviews
      our site & Booking.com
      Map
      1.0 mi from City Center254 yd from Ernest Hemingway House
      Full KitchenPicnic AreaBicycle Rental
      • Fully equipped kitchen in unit
      • Private check-in/check-out
      • Walk to Duval Street
      FromUS$ 560 /nightSelect
      Orchid Bay Condo - Pool - Old Town - Walk To DuvalApartment
      8.9
      Great37 total reviews
      our site & Booking.com
      4 adults
      1 bedroom
      2 beds
      Map
      1.1 mi from City Center517 yd from Key West Cemetery
      Outdoor PoolFull KitchenSun Terrace
      • Pool-view balcony in historic building
      • Full kitchen with private entrance
      • Year-round outdoor pool on site
      FromUS$ 660 /nightSelect
      The Bartlum-Luxurious StudioApartment
      9.0
      Perfect43 total reviews
      our site & Booking.com
      4 adults
      1 bedroom
      2 beds
      Map
      1.3 mi from City Center443 yd from San Carlos Institute Casa Cuba
      Full KitchenWasher/DryerCable TV
      • In-unit washer and dryer
      • Full kitchen with dishwasher
      • Steps to Duval Street
      FromUS$ 186 /nightSelect
      Kwss204 Sunrise Suites Barbados Suite #204Apartment
      7.7
      Very good56 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center1229 yd from Kayak Kings Key West
      Heated PoolTennis CourtHot Tub
      • Two-bedroom apartment with kitchen
      • On-site tennis court and fitness
      • Pets allowed with heated pool
      FromUS$ 208 /nightSelect
      Sea Breeze -Great Location!Holiday home
      9.2
      Perfect35 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.1 mi from City Center219 yd from Ernest Hemingway House
      Water ParkPrivate PatioFull Kitchen
      • On-site water park for family fun
      • City-view patio with private entrance
      • Steps from Hemingway Home and Museum
      FromUS$ 355 /nightSelect
      Traveler'S PalmApartment
      7.5
      Very good36 total reviews
      our site & Booking.com
      4 adults
      1 bedroom
      2 beds
      Map
      1.2 mi from City Center169 yd from Fury Water Adventures Key West
      Water ParkGolf CourseWater Sports
      • Spacious apartment with full kitchen
      • On-site water park and water sports
      • Private patio with city views
      FromUS$ 470 /nightSelect
      Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner CondoHoliday home
      9.1
      Perfect18 total reviews
      our site & Booking.com
      Map
      705 yd from City Center1033 yd from Key West Cemetery
      Outdoor PoolFree ParkingLift
      • Waterfront corner with sea views
      • Private entrance for added privacy
      • On-site water sports facilities
      FromUS$ 184 /nightSelect
      New Casa Caribe By Brightwild- Two-Story Condo Rooftop PoolHoliday home
      8.2
      Great19 total reviews
      our site & Booking.com
      Map
      1.0 mi from City Center285 yd from Ernest Hemingway House
      Rooftop PoolFree ParkingCity Views
      • Rooftop pool with city views
      • Two-story condo private entrance
      • Free private parking included
      FromUS$ 343 /nightSelect
      Cloud Suite On DuvalApartment
      9.2
      Perfect14 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center86 yd from Fury Water Adventures Key West
      Full KitchenPrivate PatioWater Sports
      • Three-bathroom apartment suite
      • On-site water sports activities
      • Private entrance and patio
      FromUS$ 1 044 /nightSelect
      Kwss310 Sunrise Suites Panama Suite #310Holiday home
      8.1
      Great58 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center1194 yd from Kayak Kings Key West
      Hot tubHeated poolTennis court
      • Private balcony with hot tub
      • 2-bedroom suite with kitchen
      • Heated outdoor swimming pool
      FromUS$ 122 /nightSelect
      Kwss210 Sunrise Suites Bonaire Suite #210Apartment
      7.5
      Very good18 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center1205 yd from Kayak Kings Key West
      Tennis CourtHeated PoolFull Kitchen
      • On-site tennis court
      • Pet-friendly apartment suites
      • Full kitchen in each suite
      FromUS$ 197 /nightSelect
      Kw353A The Coral CoveApartment
      8.1
      Great11 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center156 yd from Ernest Hemingway House
      Full KitchenCyclingRestaurant
      • Apartment with fully equipped kitchen
      • On-site cycling and fishing
      • Restaurant available on site
      FromUS$ 159 /nightSelect
      Show more

      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.