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Search results; Over 1,000 homes in Leeward Settlement

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Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 bed, 1 private bathroom
2–7 Sept
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4.89 out of 5 average rating, 156 reviews
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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
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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
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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
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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
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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
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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
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Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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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
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Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
1 bedroom, 1.5 bathrooms
3–8 Sept
4.96 out of 5 average rating, 83 reviews
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Top guest favourite
Villa in Grace Bay
Boutique Villa w Private Beach Chairs on Grace Bay
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Grace Bay
#10 The Enclave
2 bedrooms, 3 beds, 2.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Flat in Caicos Islands
Guest Apartment near Grace Bay Beach
1 bedroom, 3 beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 107 reviews
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Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.96 out of 5 average rating, 23 reviews
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Top guest favourite
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 10 reviews
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Superhost
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, 12 reviews
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Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 46 reviews
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Guest favourite
Guest house in Long bay
Villa Kendara~50% 9/26-10/3 ~Beach~Privt~Gate~View
2 bedrooms, 4 beds, 1 bathroom
26 Sept – 2 Oct
4.94 out of 5 average rating, 96 reviews