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Search results; Over 1,000 homes in Leeward Settlement

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Superhost
Guest house in Leeward Settlement
XOXO – Cottage, is a newly renovated 1 bed cottage
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
13–18 Oct
4.92 out of 5 average rating, 132 reviews
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Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds
25–30 Sept
4.91 out of 5 average rating, 58 reviews
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Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds
25–30 Sept
4.97 out of 5 average rating, 35 reviews
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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
3–8 Oct
4.94 out of 5 average rating, 97 reviews
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Guest favourite
Flat in Caicos Islands
Guest Apartment near Grace Bay Beach
1 bedroom, 3 beds
20–25 Sept
4.97 out of 5 average rating, 108 reviews
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Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds
18–23 Oct
5.0 out of 5 average rating, 34 reviews
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Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds
3–8 Oct
4.71 out of 5 average rating, 108 reviews
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Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed
19–24 Sept
4.89 out of 5 average rating, 159 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
1–6 Oct
4.9 out of 5 average rating, 73 reviews
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Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds
1–6 Oct
4.84 out of 5 average rating, 32 reviews
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Top guest favourite
Apartment in Providenciales
Modern Condo | Amazing Pool | On Site Spa
2 bedrooms, 2 queen beds
21–26 Sept
4.92 out of 5 average rating, 276 reviews
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Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds
28 Sept – 3 Oct
4.61 out of 5 average rating, 18 reviews
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Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds
19–24 Sept
4.86 out of 5 average rating, 7 reviews
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Guest favourite
Villa in Providenciales
Salt Air Villa - Canalfront, Leeward
4 bedrooms, 5 beds
20–25 Sept
4.78 out of 5 average rating, 37 reviews
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Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds
19–24 Sept
4.89 out of 5 average rating, 38 reviews
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Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds
30 Sept – 5 Oct
4.92 out of 5 average rating, 13 reviews
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Guest favourite
Home in Grace Bay
Gabriella Luxury Villa - Opening Special Rates
3 bedrooms, 3 beds
23–28 Sept
4.95 out of 5 average rating, 19 reviews