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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
4–9 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
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
1–6 Sept
4.98 out of 5 average rating, 54 reviews
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Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.89 out of 5 average rating, 38 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
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Sept
4.97 out of 5 average rating, 30 reviews
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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
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Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 9 reviews
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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
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Guest favourite
Villa in Leeward Settlement
Waterfront Luxury Villa with Pool, Dock, Kayaks
5 bedrooms, 6 beds, 5.5 bathrooms
2–7 Sept
4.96 out of 5 average rating, 24 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
1–6 Sept
4.86 out of 5 average rating, 7 reviews
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Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
30 Sept – 5 Oct
4.92 out of 5 average rating, 13 reviews
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Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
2–7 Sept
4.92 out of 5 average rating, 26 reviews
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Luxe
Villa in Leeward Settlement
Canalfront Turks & Caicos Villa w/ Infinity Pool
5 bedrooms, 7 beds, 5 bathrooms
1–6 Sept
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Superhost
Home in Caicos Islands
Harbour House - 3 Bed Waterfront; 7 Min to Beach
3 bedrooms, 4 beds, 3.5 bathrooms
2–7 Sept
4.91 out of 5 average rating, 34 reviews
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Superhost
Home in Leeward Settlement
Casa Verde - 7BR on the Canal across from Beach
7 bedrooms, 8 beds, 7.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Luxe
Villa in Long Bay Hills
Beachfront Villa w/ Infinity Pool on Long Bay
4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews