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 3 – 10
Home in Islamorada
4.94 out of 5 average rating, 17 reviews3 Lux Ensuites Walk/Boat Island!
Mar 22 – 29
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
Feb 13 – 20
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
Aug 31 – Sep 7
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Dec 14 – 21
Home in Islamorada
5.0 out of 5 average rating, 12 reviewsAngler's Reef Gem in Islamorada!
Jan 25 – Feb 1
Home in Islamorada
5.0 out of 5 average rating, 6 reviewsAnglers Reef Home with Peek-a-Boo Ocean Views
May 4 – 11
Home in Islamorada
4.96 out of 5 average rating, 57 reviewsTropical Getaway 3/3 with 100’ boat dock and pool
Oct 27 – Nov 3
Condo rentals with a pool
Condo in Tavernier
4.97 out of 5 average rating, 158 reviewsSerenity In The Sun
Mar 23 – 30
Condo in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Jan 12 – 19
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 22 – 29
Condo in Tavernier
4.88 out of 5 average rating, 112 reviewsResort Getaway : Condo, Pool, Beach, Location
Sep 20 – 27
Condo in Tavernier
4.91 out of 5 average rating, 110 reviews500 Burton Drive Tavernier, Key Largo
Jan 19 – 26
Condo in Tavernier
4.88 out of 5 average rating, 135 reviewsSpectacular 2 Bedroom with a beautiful ocean view.
Apr 16 – 23
Condo in Key Largo
4.98 out of 5 average rating, 115 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Nov 7 – 14
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
Aug 9 – 16
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
G$14,636 GYD before taxes and fees
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