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Search results; Over 1,000 homes in Leeward Settlement

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Top guest favourite
Flat in Leeward Settlement
Romantic Apartment few steps from beach
1 bedroom, 1 bed, 1 private bathroom
10–15 Nov
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4.96 out of 5 average rating, 269 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, 60 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
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Oct
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
23–28 Nov
4.92 out of 5 average rating, 133 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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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, 20 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
24–29 Oct
4.96 out of 5 average rating, 23 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
4.91 out of 5 average rating, 32 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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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
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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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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Guest favourite
Place to stay in Providenciales
Cozy room/pool in Leeward near sunset, gracebay
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 52 reviews
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Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
5–10 Oct
4.98 out of 5 average rating, 43 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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Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
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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
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