Holiday 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.
Holiday 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!
3–10 Aug
Home in Islamorada
4.94 out of 5 average rating, 17 reviews3 Lux Ensuites Walk/Boat Island!
22–29 Mar
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
13–20 Feb
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
31 Aug – 7 Sept
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
14–21 Dec
Home in Islamorada
5.0 out of 5 average rating, 12 reviewsAngler's Reef Gem in Islamorada!
25 Jan – 1 Feb
Home in Islamorada
5.0 out of 5 average rating, 6 reviewsAnglers Reef Home with Peek-a-Boo Ocean Views
4–11 May
Home in Islamorada
4.96 out of 5 average rating, 57 reviewsTropical Getaway 3/3 with 100’ boat dock and pool
27 Oct – 3 Nov
Apartment rentals with a pool
Apartment in Tavernier
4.97 out of 5 average rating, 158 reviewsSerenity In The Sun
23–30 Mar
Apartment in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
12–19 Jan
Apartment in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Aug
Apartment in Tavernier
4.91 out of 5 average rating, 110 reviews500 Burton Drive Tavernier, Key Largo
19–26 Jan
Apartment in Tavernier
4.88 out of 5 average rating, 112 reviewsResort Getaway : Condo, Pool, Beach, Location
20–27 Sept
Apartment in Key Largo
4.98 out of 5 average rating, 115 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
7–14 Nov
Apartment in Tavernier
4.88 out of 5 average rating, 135 reviewsSpectacular 2 Bedroom with a beautiful ocean view.
16–23 Apr
Apartment in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
9–16 Aug
Quick stats about holiday 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
£56 before taxes and fees
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