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 Colony Beach
4.98 out of 5 average rating, 110 reviewsSuper Nov. Savings! Key Colony Beach, Cabana Club
Home in Key Largo
4.96 out of 5 average rating, 124 reviewsTiny Home on Waterfront | Bay Views | Deck | Pool
Home in Key Largo
4.91 out of 5 average rating, 148 reviewsBlue House Marine in Key Largo
Home in Marathon
4.95 out of 5 average rating, 124 reviewsParadise - Pool, Hot tub, Mini Golf, Dockage, Fish
Home in Key Largo
4.87 out of 5 average rating, 109 reviewsParadise Palace 3/3 Waterfront Pool Kayak 60' Dock
Home in Marathon
5 out of 5 average rating, 8 reviewsSalt & Seaglass. XL Screen Porch, Dock, Pool club!
Home in Marathon
4.98 out of 5 average rating, 132 reviewsMarathon one-level home on the Marina - with slip!
Home in Key Colony Beach
4.91 out of 5 average rating, 137 reviewsTiki Time 2
Condo rentals with a pool
Condo in Tavernier
4.9 out of 5 average rating, 124 reviews1BR - Key Largo Sun & Sand Hideaway
Condo in Tavernier
4.87 out of 5 average rating, 139 reviewsReel Large END Unit in Ocean Point Suites
Condo in Tavernier
4.89 out of 5 average rating, 119 reviews500 Burton Drive Tavernier, Key Largo
Condo in Key Largo
4.99 out of 5 average rating, 103 reviewsEnjoy sunsets & sunrise in your home away home.
Condo in Key Largo
4.87 out of 5 average rating, 146 reviewsTropical Getaway
Condo in Tavernier
4.89 out of 5 average rating, 143 reviewsSpectacular 2 Bedroom with a beautiful ocean view.
Condo in Tavernier
4.93 out of 5 average rating, 122 reviewsKeys Life Ocean Pointe Pool Jacuzzi Beach Crib
Condo in Key Colony Beach
4.92 out of 5 average rating, 130 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Quick stats about vacation rentals with a pool in Islamorada
Total rentals
640 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
430 properties are a good fit for families
Pet-friendly rentals
290 properties allow pets
Rentals with dedicated workspaces
380 properties have a dedicated workspace
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