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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
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4.91 out of 5 average rating, 158 reviews
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
5 bedrooms, 7 beds
3–8 Jul
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds
13–18 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds
3–8 Jul
4.98 out of 5 average rating, 52 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds
1–6 Jul
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds
2–7 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds
1–6 Aug
4.96 out of 5 average rating, 23 reviews
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
4 bedrooms, 5 beds
1–6 Jul
5.0 out of 5 average rating, 4 reviews
Villa in Leeward Settlement
Aqua Divina Villas
5 bedrooms, 8 beds
1–6 Jul
4.67 out of 5 average rating, 12 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 beds
12–17 Jul
4.9 out of 5 average rating, 52 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds
4–9 Jul
5.0 out of 5 average rating, 45 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds
1–6 Jul
4.84 out of 5 average rating, 32 reviews
Guest favourite
Villa in Providenciales
Salt Air Villa - Canalfront, Leeward
4 bedrooms, 5 beds
25–30 Aug
4.77 out of 5 average rating, 35 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
15–20 Aug
4.92 out of 5 average rating, 128 reviews
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
4 bedrooms, 4 beds
1–6 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Leeward Settlement
Leeward Jewel Villa - Luxurious 7 bedroom Canal Fr
7 bedrooms, 8 beds
3–8 Jul
5.0 out of 5 average rating, 11 reviews
Villa in Grace Bay
Villa Rise
4 bedrooms
1–6 Jul
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
4 bedrooms, 7 beds
6–11 Jul
5.0 out of 5 average rating, 9 reviews