Leeward Settlement vacation rentals
We found 1,135 vacation rentals — enter your dates for availability
Discover a selection of 60 homes, 160 villas, and vacation rentals in Leeward Settlement that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
Find the best place to stay - Leeward Settlement
Ocean Dream 5 BR Villa Aqua - Oceanfront
Sleeps 11 · 5 bedrooms · 4+ bathrooms
Find spaces that suit your style
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Top rated rentals - Leeward Settlement
Photo gallery for Beachfront, 3 BR end-unit with incredible views of the ocean and beach.
Unforgettable Paradise
- 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