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Search results; Over 1,000 homes in Leeward Settlement

Descriptions are based on details hosts provide
Villa in Leeward Settlement
Our Home on the Water - I Land Time Villa
2 bedrooms, 3 beds, 1.5 private bathrooms
16–21 Jul
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4.75 out of 5 average rating, 16 reviews
Top guest favourite
Villa in Leeward Settlement
Waterfront villa with concierge and dock
5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Leeward Settlement
Canal-front home with a floating dock
3 bedrooms, 6 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Leeward Settlement
Newly built with pool near Grace Bay
3 bedrooms, 3 beds, 3.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 18 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Leeward Settlement
Canal-front villa with a glass-edge pool
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Jul
4.92 out of 5 average rating, 24 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
15–20 Jul
4.92 out of 5 average rating, 130 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Villa in Providenciales
Waterfront with a swim-up bar
5 bedrooms, 7 beds, 3.5 bathrooms
15–20 Jul
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Villa in Leeward Settlement
Pool, putting green, and bocce near beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
4.96 out of 5 average rating, 24 reviews
Luxe
Home in Leeward Settlement
Canal-front estate with infinity pool and dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 30 reviews
Superhost
Villa in Providenciales
Gated villa with daily housekeeping and pool
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Jul
4.84 out of 5 average rating, 32 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
4.9 out of 5 average rating, 52 reviews
Superhost
Home in Leeward Settlement
Gated villa with pool near Grace Bay
3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
Guest favourite
Villa in Caicos Islands
New villa with pool near Grace Bay
4 bedrooms, 4 king beds, 4 bathrooms
2–7 Aug
4.94 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Leeward
Canal access with kayaks near Grace Bay
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Home in 144645
New build with a private pool
4 bedrooms, 7 beds, 3.5 bathrooms
15–20 Jul
4.76 out of 5 average rating, 17 reviews
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
4.9 out of 5 average rating, 69 reviews