Holiday rentals with a pool in Summerland Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Summerland Key
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Summerland Key rentals with a pool
House rentals with a pool
Home in Cudjoe Key
4.81 out of 5 average rating, 124 reviewsOcean View 2/2 on Canal
19–26 Aug
Home in Key Colony Beach
4.96 out of 5 average rating, 134 reviewsBeautiful open plan remodeled home in Key Colony
23–30 Oct
Home in Summerland Key
4.83 out of 5 average rating, 6 reviewsBungalows at Sugarloaf Beach - Little Hammock
18–25 May
Home in Cudjoe Key
4.86 out of 5 average rating, 42 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
10–17 Oct
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
30 Nov – 7 Dec
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
18–25 Aug
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
30 Sep – 7 Oct
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
15–22 Apr
Apartment rentals with a pool
Apartment in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Aug
Apartment in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
8–15 Dec
Apartment in Key West
4.93 out of 5 average rating, 118 reviewsDowntown 4/4 Waterfront Penthouse Pool, Dock, Pet
22–29 May
Apartment in Marathon
4.87 out of 5 average rating, 191 reviewsSombrero Beach Tropical Getaway
17–24 Oct
Apartment in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
31 May – 7 Jun
Apartment in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
30 Aug – 6 Sep
Apartment in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
29 Sep – 6 Oct
Apartment in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
15–22 Sep
Quick stats about holiday rentals with a pool in Summerland Key
Total rentals
140 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
3.2K reviews
Nightly prices starting at
€ 103 before taxes and fees
Destinations to explore
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