Leeward Islands rentals with pool
We found 40 rentals with pool — enter your dates for availability
Explore Leeward Islands rentals with pools

Seaside house, 300° sea view, private lagoon access. 2 /6 p, (possibility 8p).
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.0 out of 10
very good
(4 reviews)
Top rated rentals with pools - Leeward Islands

Relaxing family getaway
10 out of 10
exceptional
(7 reviews)
Perfect for our family with teens. The pool was great and the kitchen ideal for any meals. Well equipped shop at the bottom of the drive. Close to all the great spots yet far enough away too. Lovely owners, very helpful. Thank you!
Rachel P.
Stayed Jan 2023
Find spaces that suit your style
House
Condo/Apartment