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 Marathon
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
20–27 Apr
Home in Summerland Key
4.86 out of 5 average rating, 7 reviewsBungalows at Sugarloaf Beach - Little Hammock
30 Aug – 6 Sep
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
22–29 Mar
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
7–14 Dec
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
16–23 Dec
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
11–18 Dec
Home in Cudjoe Key
4.88 out of 5 average rating, 73 reviewsIsland Oasis ~ YOUR Paradise Awaits!
23–30 Mar
Home in Cudjoe Key
4.82 out of 5 average rating, 11 reviewsRise-N-Shine
18–25 Apr
Condo rentals with a pool
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
3–10 Oct
Condo in Key West
4.88 out of 5 average rating, 147 reviewsLarge waterfront 2/2 end unit with boat slip
7–14 Mar
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Aug
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
22–29 Oct
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
7–14 Oct
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
2–9 Sep
Condo in Tavernier
4.99 out of 5 average rating, 102 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
21–28 Sep
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
20–27 Apr
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
$184 NZD before taxes and fees
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