Vacation 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.
Vacation 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
Jul 12 – 19
Home in Marathon
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
Dec 20 – 27
Home in Summerland Key
4.86 out of 5 average rating, 7 reviewsBungalows at Sugarloaf Beach - Little Hammock
Dec 7 – 14
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Jan 13 – 20
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Jan 6 – 13
Home in Cudjoe Key
4.87 out of 5 average rating, 45 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Mar 3 – 10
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Oct 8 – 15
Home in Cudjoe Key
4.83 out of 5 average rating, 12 reviewsRise-N-Shine
Feb 9 – 16
Condo rentals with a pool
Condo in Key West
4.86 out of 5 average rating, 130 reviewsA Perfect Getaway
Jul 20 – 27
Condo in Key West
4.89 out of 5 average rating, 148 reviewsLarge waterfront 2/2 end unit with boat slip
Mar 22 – 29
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Oct 27 – Nov 3
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
Nov 10 – 17
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Sep 21 – 28
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Apr 1 – 8
Condo in Tavernier
4.99 out of 5 average rating, 102 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Sep 7 – 14
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
Apr 22 – 29
Quick stats about vacation 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
ﺩ.ﺇ404 before taxes and fees
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