Vacation rentals with a pool in Big Pine Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Big Pine 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 Big Pine Key rentals with a pool
House rentals with a pool
Home in Cudjoe Key
4.9 out of 5 average rating, 104 reviewsSunrise Beach Escape
Home in Key Colony Beach
4.9 out of 5 average rating, 134 reviewsTiki Time 2
Home in Cudjoe Key
4.81 out of 5 average rating, 224 reviewsOCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Home in Marathon
4.97 out of 5 average rating, 34 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Home in Key Colony Beach
4.95 out of 5 average rating, 80 reviewsWaterfront Home 37.5-ft dock, Cabana Club Included
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviews“La casa azul” step 3’ to a private pool
Home in Marathon
5.0 out of 5 average rating, 4 reviewsP31 - 11785 5th Ave. Ocean
Home in Cudjoe Key
4.87 out of 5 average rating, 46 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Condo rentals with a pool
Condo in Key West
4.93 out of 5 average rating, 134 reviewsBeach Club Ocean Front 2BR Condo
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 West
4.86 out of 5 average rating, 131 reviewsA Perfect Getaway
Condo in Key West
4.89 out of 5 average rating, 150 reviewsLarge waterfront 2/2 end unit with boat slip
Condo in Tavernier
4.88 out of 5 average rating, 229 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH 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
4.98 out of 5 average rating, 144 reviewsOcean Views at Ocean Pointe
Quick stats about vacation rentals with a pool in Big Pine Key
Total rentals
100 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
2.5K reviews
Nightly prices starting at
$80 before taxes and fees
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