Leeward rentals with pool

We found 1,310 rentals with pool — enter your dates for availability

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September 2025

13

October 2025

Explore Leeward rentals with pools

Pool

Sunrock 2BR in Colombier by Personal Villas - Sundeck, Swimming Pool, Jacuzzi

Sleeps 4 · 2 bedrooms · 2 bathrooms

Room

Premier Host

Villa Rosebud, 2BR, 2BA, (Sleeps 2-4), on the beach of Anse Des Cayes

Sleeps 4 · 2 bedrooms · 2 bathrooms

Pool

🏝REAL BEACH VILLA ON THE BEACH !🏝CLOSE TO FLAMANS-ST JEAN BEACH CITY.REST.BARS

Sleeps 6 · 3 bedrooms · 3 bathrooms

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