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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Flat in Leeward Settlement
Romantic Apartment few steps from beach
1 bedroom, 1 bed, 1 private bathroom
7–12 Aug
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4.96 out of 5 average rating, 267 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
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 34 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
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
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
Home in Providenciales
NEW - Aqua Blu Beachfront Villa "The Palm"
4 bedrooms, 4 king beds, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
7–12 Aug
4.97 out of 5 average rating, 34 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
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
30 Sept – 5 Oct
4.91 out of 5 average rating, 11 reviews
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
3 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
New place to stay
Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
7–12 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 88 reviews
Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 7 reviews