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Search results; Over 1,000 homes in Leeward Settlement

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Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Oct
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4.97 out of 5 average rating, 35 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
1–6 Oct
4.92 out of 5 average rating, 59 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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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, 133 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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Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Villa in Leeward Settlement
Luxury Canal Front Villa Kayaks, Pool & BBQ
8 bedrooms, 9 beds, 7.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 9 reviews
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Superhost
Home in Providenciales
Grace Bay, Pool, Great Reviews! (#2,3)
6 bedrooms, 8 beds, 8 bathrooms
19–24 Oct
4.74 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, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 98 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
1–6 Oct
4.9 out of 5 average rating, 31 reviews
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Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Oct
4.61 out of 5 average rating, 18 reviews
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Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
4.92 out of 5 average rating, 13 reviews
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Superhost
Home in Grace Bay
25% Off September! Walk To Beach W/Private Pool
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
31 Oct – 5 Nov
4.96 out of 5 average rating, 23 reviews
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Superhost
Home in Leeward Settlement
Blue Tang Villa Estate (7 Bedroom)
7 bedrooms, 8 beds, 7.5 bathrooms
20–25 Oct
4.69 out of 5 average rating, 16 reviews
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Guest favourite
Home in Grace Bay
Gabriella Luxury Villa - Opening Special Rates
3 bedrooms, 3 beds, 4.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Villa in Caicos Islands
Modern 4BR oasis on 1 acre, 1 min from the Beach
4 bedrooms, 5 beds, 3.5 bathrooms
11–16 Oct
4.92 out of 5 average rating, 111 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 Oct
4.97 out of 5 average rating, 30 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 Oct
5.0 out of 5 average rating, 8 reviews