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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Guest suite in Leeward Settlement
The Sandbox (UNIT 1)
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.99 out of 5 average rating, 96 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
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, 4 bathrooms
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 34 reviews
Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
5.0 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
1–6 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Sept
4.84 out of 5 average rating, 32 reviews
Home in Providenciales
NEW - Aqua Blu Beachfront Villa "The Orchid"
4 bedrooms, 4 beds, 5 bathrooms
1–6 Sept
New place to stay
Guest favourite
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
15–20 Sept
4.86 out of 5 average rating, 7 reviews
Luxe
Villa in Leeward Settlement
*Brand-new* Villa Terra Blue - Walk to Beach
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms, 6 beds, 5.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Luxe
Villa in Leeward Settlement
Sunset Bay Villa - 10 mins away from Grace Bay
5 bedrooms, 5 beds, 5.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
12–17 Sept
4.9 out of 5 average rating, 29 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
4.89 out of 5 average rating, 155 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.61 out of 5 average rating, 18 reviews
Guest favourite
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Sept
4.9 out of 5 average rating, 31 reviews