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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
21–26 Aug
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4.98 out of 5 average rating, 54 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
21–26 Aug
4.92 out of 5 average rating, 132 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 34 reviews
Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds
22–27 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds
29 Aug – 3 Sept
4.97 out of 5 average rating, 34 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds
27 Aug – 1 Sept
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds
30 Aug – 4 Sept
4.88 out of 5 average rating, 8 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds
12–17 Sept
4.9 out of 5 average rating, 29 reviews
Guest house in Long Bay Hills
Twins Villa – Mellizo A | Poolside Unit, Long Bay
2 bedrooms, 2 beds
21–26 Aug
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds
21–26 Aug
5.0 out of 5 average rating, 34 reviews
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
5 bedrooms, 7 beds
23–28 Aug
4.99 out of 5 average rating, 68 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds
30 Sept – 5 Oct
4.91 out of 5 average rating, 11 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds
22–27 Aug
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Home in Leeward Settlement
PERIWINKLE | Charming Island Home|Near to Beach
2 bedrooms, 2 beds
21–26 Aug
4.96 out of 5 average rating, 98 reviews
Villa in Providenciales
NEW - Aqua Blu Beachfront Villa "The Jasmine"
4 bedrooms, 4 king beds
26–31 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds
21–26 Aug
4.96 out of 5 average rating, 23 reviews
Superhost
Villa in Leeward Settlement
Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews