Typical bungalow at the Four Seasons. Over 1000 square feet of Polynesian luxury all to yourself. No compromises on quality here, and the service is impeccable.

Hop into the lagoon from your own private deck! Not much to see in the way of fish or coral, but great for swimming or just hanging out (the water by our bungalow was only waist deep).

My only nit is the $20/day they charge for WiFi in your room - feels like nickel-and-diming given the $1000/night room rate.

Photo by Mark Rentz

Leeward Islands rentals with pool

We found 45 rentals with pool — enter your dates for availability

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December 2025

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January 2026

Explore Leeward Islands rentals with pools

Pool

Cozy Oceanfront Villa with Private Pool & Stunning Moonrise Views

Sleeps 3 · 1 bedroom · 1 bathroom

Pool

Unique luxuous 350sq m Villa with pool, fitness area, home cinema lounge ....

Sleeps 6 · 3 bedrooms · 2+ bathrooms

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