Vacation rentals with a pool in Windley Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Windley Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windley Key rentals with a pool
House rentals with a pool
Home in Key Largo
4.9 out of 5 average rating, 127 reviewsBlue House Marine in Key Largo
Jan 15 – 22
Home in Marathon
4.99 out of 5 average rating, 107 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Sep 14 – 21
Home in Key Largo
4.95 out of 5 average rating, 106 reviewsMariners Club Resort, Best in the Upper Keys
Oct 12 – 19
Home in Marathon
4.97 out of 5 average rating, 119 reviewsMarathon one-level home on the Marina - with slip!
Dec 20 – 27
Home in Key Largo
4.86 out of 5 average rating, 103 reviewsParadise Palace 3/3 Waterfront Pool Kayak 60' Dock
Jul 2 – 9
Home in Key Largo
4.88 out of 5 average rating, 165 reviewsOutdoor Paradise - Beach, Boats, Snorkeling & Sun!
Oct 23 – 30
Home in Islamorada
5.0 out of 5 average rating, 6 reviewsAnglers Reef Home with Peek-a-Boo Ocean Views
Feb 1 – 8
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
Aug 17 – 24
Condo rentals with a pool
Condo in Key Largo
4.98 out of 5 average rating, 117 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Nov 2 – 9
Condo in Tavernier
4.87 out of 5 average rating, 126 reviewsReel Large END Unit in Ocean Point Suites
Oct 9 – 16
Condo in Tavernier
4.93 out of 5 average rating, 108 reviewsKeys Life Ocean Pointe Pool Jacuzzi Beach Crib
Feb 11 – 18
Condo in Key Largo
4.97 out of 5 average rating, 148 reviewsKEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!
Nov 11 – 18
Condo in Tavernier
4.88 out of 5 average rating, 110 reviews1BR - Keys Paradise Hideaway
Oct 16 – 23
Condo in Tavernier
4.8 out of 5 average rating, 130 reviewsTROPICAL PARADISE Ocean Condo - Cabana Daydreamin'
Oct 28 – Nov 4
Condo in Tavernier
4.83 out of 5 average rating, 179 reviewsToes in the Sand - 2 Bedroom Condo Sleeps 4
Aug 9 – 16
Condo in Tavernier
4.88 out of 5 average rating, 113 reviewsResort Getaway : Condo, Pool, Beach, Location
Apr 10 – 17
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