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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Flat in Leeward Settlement
Leisure in Paradise - steps from Beach, with pool
1 bedroom, 2 beds, 1 private bathroom
5–10 Aug
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4.95 out of 5 average rating, 299 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
4.92 out of 5 average rating, 130 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
16–21 Aug
4.91 out of 5 average rating, 54 reviews
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
4.89 out of 5 average rating, 28 reviews
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Aug
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
6–11 Aug
4.92 out of 5 average rating, 25 reviews
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 7 reviews
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
New place to stay
Guest favourite
Villa in Leeward Settlement
Waterfront Luxury Villa with Pool & Private Dock
5 bedrooms, 6 beds, 5.5 bathrooms
6–11 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Leeward Settlement
PERIWINKLE | Charming Island Home|Near to Beach
2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
4.96 out of 5 average rating, 98 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
11–16 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
18–23 Aug
4.98 out of 5 average rating, 54 reviews
Guest house in Long Bay Hills
Twins Villa – Mellizo A | Poolside Unit, Long Bay
2 bedrooms, 2 beds, 2 bathrooms
5–10 Aug