Holiday 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.
Holiday rentals for every style
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Popular amenities for Monroe County rentals with a pool
House rentals with a pool
Home in Cudjoe Key
4.97 out of 5 average rating, 121 reviewsCudjoe Key Home with a View
7–14 Oct
Home in Marathon
4.97 out of 5 average rating, 117 reviewsMarathon one-level home on the Marina - with slip!
22–29 May
Home in Miami
5.0 out of 5 average rating, 236 reviewsModern,spacious Retreat !Salt water,heated pool!
17–24 Oct
Home in Cudjoe Key
4.9 out of 5 average rating, 104 reviewsSunrise Beach Escape
17–24 Jan
Home in Marathon
4.99 out of 5 average rating, 106 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
24–31 Aug
Home in Homestead
4.93 out of 5 average rating, 357 reviewsPrivate Paradise between Miami & the Keys
27 Mar – 3 Apr
Home in Key Colony Beach
4.96 out of 5 average rating, 134 reviewsBeautiful open plan remodeled home in Key Colony
23–30 Oct
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
20–27 Mar
Apartment rentals with a pool
Apartment in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
31 May – 7 Jun
Apartment in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Aug
Apartment in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
30 Aug – 6 Sep
Apartment in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
29 Sep – 6 Oct
Apartment in Key West
4.93 out of 5 average rating, 132 reviewsBeach Club Ocean Front 2BR Condo
1–8 Dec
Apartment in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
8–15 Dec
Apartment in Miami
4.92 out of 5 average rating, 161 reviewsHeart of Coconut Grove, pool. gym/sauna, park free
22–29 Jun
Apartment in Tavernier
4.93 out of 5 average rating, 133 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
24–31 Jan
Destinations to explore
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