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
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Popular amenities for Monroe County rentals with a pool
House rentals with a pool
Home in Marathon
4.97 out of 5 average rating, 119 reviewsMarathon one-level home on the Marina - with slip!
Dec 20 – 27
Home in Cudjoe Key
4.97 out of 5 average rating, 124 reviewsCudjoe Key Home with a View
Oct 10 – 17
Home in Cudjoe Key
4.9 out of 5 average rating, 104 reviewsSunrise Beach Escape
Aug 10 – 17
Home in Key Largo
4.97 out of 5 average rating, 109 reviewsTiny Home on Waterfront | Bay Views | Deck | Pool
Feb 13 – 20
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 Key Largo
4.9 out of 5 average rating, 127 reviewsBlue House Marine in Key Largo
Jan 15 – 22
Home in Homestead
4.93 out of 5 average rating, 358 reviewsPrivate Paradise between Miami & the Keys
Aug 27 – Sep 3
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
Aug 17 – 24
Condo rentals with a pool
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
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 Key West
4.86 out of 5 average rating, 130 reviewsA Perfect Getaway
Jul 20 – 27
Condo in Tavernier
4.93 out of 5 average rating, 136 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Feb 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
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