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Search results; Over 1,000 homes in Leeward Settlement

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Leeward Settlement
"The Nest Cozy Cottage"
1 bedroom, 1 bed, 1 private bathroom
15–20 Jul
,
4.98 out of 5 average rating, 130 reviews
Guest favourite
Villa in Leeward Settlement
Beachfront with a swim-up bar
4.92 out of 5 average rating, 130 reviews, 3 bedrooms, 3 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Villa in Leeward Settlement
Waterfront villa with concierge and dock
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4.9 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Top guest favourite
Villa in Leeward Settlement
Pool, putting green, and bocce near beach
4.96 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
4.94 out of 5 average rating, 88 reviews, 2 bedrooms, 5 beds, 2 bathrooms
28 Jul – 3 Aug
Guest favourite
Villa in Leeward Settlement
Newly built with pool near Grace Bay
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
15–20 Jul
Guest favourite
Villa in Leeward Settlement
Live style villa
4.89 out of 5 average rating, 37 reviews, 4 bedrooms, 4 beds, 3 bathrooms
20–25 Jul
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 6 beds, 4 bathrooms
5–10 Aug
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4.95 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 3 bathrooms
27 Aug – 1 Sept
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.9 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Guest favourite
Villa in Leeward Settlement
Waterfront villa with canal access and pool
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Home in Providenciales
Private pool with Chalk Sound views
5.0 out of 5 average rating, 44 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
27 Jul – 1 Aug
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
Villa in Leeward Settlement
Waterfront with a dock and saltwater pool
4 bedrooms, 4 beds, 5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Villa in Venetian Road Settlement
Luxury waterfront villa with panoramic views
5.0 out of 5 average rating, 68 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Jul – 1 Aug