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Search results; Over 1,000 homes in Leeward Settlement

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Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 beds, 3.5 private bathrooms
20–25 Sept
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4.86 out of 5 average rating, 7 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
25–30 Sept
4.91 out of 5 average rating, 58 reviews
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Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
13–18 Oct
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
25–30 Sept
4.97 out of 5 average rating, 35 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
18–23 Oct
5.0 out of 5 average rating, 34 reviews
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Villa in Leeward Settlement
Piccolo Ponte | 3 BR Canal Front | Pool & Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
New place to stay
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Guest favourite
Guest house in Long bay
Villa Kendara~SALE~OCT 3-10~Beach~Privt~Gated~View
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 98 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
26 Sept – 1 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Flat in Caicos Islands
Guest Apartment near Grace Bay Beach
1 bedroom, 3 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 108 reviews
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Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds, 2 bathrooms
3–8 Oct
4.71 out of 5 average rating, 108 reviews
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Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 73 reviews
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Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.61 out of 5 average rating, 18 reviews
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Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
4.89 out of 5 average rating, 38 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
28 Sept – 3 Oct
4.9 out of 5 average rating, 31 reviews
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Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 159 reviews
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Luxe
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
8–13 Oct
4.91 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Home in Leeward Settlement
Villa Enandi
5 bedrooms, 6 beds, 5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Villa in Leeward Settlement
Leeward Jewel Villa - Luxurious 7 bedroom Canal Fr
7 bedrooms, 8 beds, 7 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 11 reviews