Vacation rentals with a pool in Monroe County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Monroe County
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 Monroe County rentals with a pool
House rentals with a pool
Home in Key Largo
4.97 out of 5 average rating, 111 reviewsTiny Home on Waterfront | Bay Views | Deck | Pool
Home in Cudjoe Key
4.97 out of 5 average rating, 124 reviewsCudjoe Key Home with a View
Home in Marathon
4.99 out of 5 average rating, 108 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Home in Key Colony Beach
4.96 out of 5 average rating, 136 reviewsBeautiful open plan remodeled home in Key Colony
Home in Homestead
4.93 out of 5 average rating, 358 reviewsPrivate Paradise between Miami & the Keys
Home in Key Largo
5.0 out of 5 average rating, 52 reviewsThe Paradise 2
Home in Marathon
4.98 out of 5 average rating, 85 reviewsAnglers Terrace, Condé Nast Traveler's Best Airbnb
Home in Marathon
4.97 out of 5 average rating, 34 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Condo rentals with a pool
Condo in Tavernier
4.98 out of 5 average rating, 144 reviewsOcean Views at Ocean Pointe
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Condo in Tavernier
4.96 out of 5 average rating, 160 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Condo in Key Colony Beach
4.91 out of 5 average rating, 114 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Condo in Key West
4.93 out of 5 average rating, 134 reviewsBeach Club Ocean Front 2BR Condo
Condo in Tavernier
4.93 out of 5 average rating, 137 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Condo in Tavernier
4.99 out of 5 average rating, 102 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Condo in Key West
4.86 out of 5 average rating, 131 reviewsA Perfect Getaway
Destinations to explore
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