Vacation rentals with a pool in Sugarloaf Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sugarloaf Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Sugarloaf 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 29 – Aug 5
Home in Marathon
4.99 out of 5 average rating, 107 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Sep 14 – 21
Home in Marathon
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
May 25 – Jun 1
Home in Key West
4.9 out of 5 average rating, 126 reviewsRoyal Escape
Oct 9 – 16
Home in Upper Sugarloaf Key
4.87 out of 5 average rating, 46 reviewsBungalows at Sugarloaf Beach - The Lighthouse
Oct 20 – 27
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
Dec 7 – 14
Home in Cudjoe Key
4.87 out of 5 average rating, 45 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Dec 1 – 8
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Apr 25 – May 2
Condo rentals with a pool
Condo in Key Colony Beach
4.96 out of 5 average rating, 171 reviewsOceanfront Sunrise Condo Private Beach Heated Pool
Sep 1 – 8
Condo in Key West
4.89 out of 5 average rating, 148 reviewsLarge waterfront 2/2 end unit with boat slip
Apr 25 – May 2
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Nov 13 – 20
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Sep 25 – Oct 2
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Mar 10 – 17
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Jan 28 – Feb 4
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
Nov 10 – 17
Condo in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Feb 12 – 19
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