Windward vacation rentals
We found 2,032 vacation rentals — enter your dates for availability
Discover a selection of 108 homes, 1940 villas, and vacation rentals in Windward that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, like cable TV and a washer and dryer. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
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Find properties near top attractions in Windward
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Find the best place to stay - Windward
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
Sleeps 6 · 3 bedrooms · 3+ bathrooms
Top rated rentals - Windward
Photo gallery for Bungalow CAZ A Saline N°2
Perfect Bungalow for a Couple
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Choose a vacation rental for your Windward getaway
Experience the unique character of Windward with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.
Exploring the natural features in Windward
Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Windward is a great place to get outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:
- Lorient Beach (0.7 mi / 1.2 km)
- Gouverneur Beach (1.4 mi / 2.3 km)
- St. Jean Beach (1.6 mi / 2.6 km)
- Flamands Beach (3.2 mi / 5.1 km)
- Colombier Beach (3.8 mi / 6.1 km)
- Dawn Beach (16.8 mi / 27 km)