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 Key Colony Beach
4.88 out of 5 average rating, 113 reviewsTiki Time
Sep 22 – 29
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Apr 26 – May 3
Home in Cudjoe Key
4.86 out of 5 average rating, 42 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Oct 10 – 17
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
Aug 31 – Sep 7
Home in Big Pine Key
4.89 out of 5 average rating, 63 reviewsFishermen`s Paradise
Dec 4 – 11
Home in Marathon
4.97 out of 5 average rating, 36 reviewsWaterfront Private Home w/Pool-Family&Pet Friendly
Nov 10 – 17
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviews“La casa azul” step 3’ to a private pool
Jul 2 – 9
Home in Little Torch Key
4.88 out of 5 average rating, 57 reviewsWaterfront Beach House with Dock & Heated Pool!
Apr 25 – May 2
Condo rentals with a pool
Condo in Key West
4.93 out of 5 average rating, 132 reviewsBeach Club Ocean Front 2BR Condo
Dec 1 – 8
Condo in Marathon
4.87 out of 5 average rating, 191 reviewsSombrero Beach Tropical Getaway
Oct 17 – 24
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
Dec 8 – 15
Condo in Key West
4.88 out of 5 average rating, 147 reviewsLarge waterfront 2/2 end unit with boat slip
Apr 14 – 21
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Aug 30 – Sep 6
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
May 31 – Jun 7
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Sep 29 – Oct 6
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Sep 15 – 22
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
R1,504 ZAR before taxes and fees
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