Vacation rentals with a pool in Islamorada
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Islamorada
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 Islamorada rentals with a pool
House rentals with a pool
Home in Key Largo
4.88 out of 5 average rating, 163 reviewsOutdoor Paradise - Beach, Boats, Snorkeling & Sun!
Aug. 2 – 9
Home in Marathon
4.97 out of 5 average rating, 32 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Dec. 7 – 14
Home in Islamorada
4.94 out of 5 average rating, 17 reviews3 Lux Ensuites Walk/Boat Island!
Mar. 22 – 29
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
Aug. 31 – Sep. 7
Home in Key Largo
5.0 out of 5 average rating, 49 reviewsThe Paradise 2
Mar. 20 – 27
Home in Islamorada
5.0 out of 5 average rating, 12 reviewsAngler's Reef Gem in Islamorada!
Jun. 8 – 15
Home in Islamorada
5.0 out of 5 average rating, 15 reviewsPristine pool front home w/ocean views Anglers 148
May 10 – 17
Home in Islamorada
5.0 out of 5 average rating, 10 reviewsHeart of Islamorada ~ Private Boat Slip
Oct. 15 – 22
Condo rentals with a pool
Condo in Tavernier
4.93 out of 5 average rating, 133 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Dec. 13 – 20
Condo in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Dec. 13 – 20
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Oct. 22 – 29
Condo in Tavernier
4.91 out of 5 average rating, 110 reviews500 Burton Drive Tavernier, Key Largo
Dec. 6 – 13
Condo in Key Largo
4.98 out of 5 average rating, 115 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Aug. 5 – 12
Condo in Tavernier
4.88 out of 5 average rating, 135 reviewsSpectacular 2 Bedroom with a beautiful ocean view.
Jan. 5 – 12
Condo in Tavernier
4.88 out of 5 average rating, 112 reviewsResort Getaway : Condo, Pool, Beach, Location
Aug. 14 – 21
Condo in Tavernier
4.87 out of 5 average rating, 125 reviewsReel Large END Unit in Ocean Point Suites
Aug. 19 – 26
Quick stats about vacation rentals with a pool in Islamorada
Total rentals
640 properties
Rentals with dedicated workspaces
430 properties have a dedicated workspace
Pet-friendly rentals
330 properties allow pets
Family-friendly rentals
440 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
$96 CAD before taxes and fees
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