Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest house in Leeward Settlement
Pelican Cottage -Mins. to the Beach!
Studio, 1 private bathroom
1–6 Jul
,
4.91 out of 5 average rating, 158 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, No bathroom
3–8 Jul
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
4.98 out of 5 average rating, 65 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
3–8 Jul
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.89 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.96 out of 5 average rating, 23 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
1–6 Jul
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4.9 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 6 beds, 2 bathrooms
4–9 Jul
Villa in Leeward Settlement
Aqua Divina Villas
4.67 out of 5 average rating, 12 reviews, 5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Jul
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Jul
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
4.84 out of 5 average rating, 32 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Jul
Guest favourite
Villa in Providenciales
Salt Air Villa - Canalfront, Leeward
4.77 out of 5 average rating, 35 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
25–30 Aug
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
4.92 out of 5 average rating, 129 reviews, 3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
Villa in Grace Bay
Villa Rise
4.83 out of 5 average rating, 6 reviews, 4 bedrooms, 3.5 bathrooms
2–7 Jul
Luxe
Villa in Providenciales
Aqueous: Luxury Villa w/Tranquil Pool Near Beach
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Jul
Top guest favourite
Villa in Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
6–11 Jul