Windward rentals with pool

We found 2,208 rentals with pool — enter your dates for availability

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September 2025

13

October 2025

Explore Windward rentals with pools

Beach

Romantic Overseas Cottage

Sleeps 3 · 1 bedroom · 1 bathroom

Beach

Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

Sleeps 2 · 1 bedroom · 1 bathroom

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Holiday rentals with spa pool in Windward

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