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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest suite in Leeward Settlement
Handfield's Hideaway Cozy One Bedrm
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.92 out of 5 average rating, 102 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
4.89 out of 5 average rating, 150 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Flat in Leeward Settlement
Luxury Paradise 1 Bedroom condo+pool in Grace Bay
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
4.97 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
Superhost
Flat in Grace Bay
25%Off July 30&31 Walk To Beach Ocean Views Z-B304
4.74 out of 5 average rating, 78 reviews, 1 bed, 1 bathroom
26 Sept – 1 Oct
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
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
4.92 out of 5 average rating, 130 reviews, 3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
Top guest favourite
Room in Leeward Settlement
Minutes from Grace Bay
5.0 out of 5 average rating, 11 reviews, 1 queen bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
11–16 Aug
Guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Apartment in Providenciales
*Blue Oasis TCI* Sun, Sand & Poolside Perfection
5.0 out of 5 average rating, 43 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Aug
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
4.96 out of 5 average rating, 79 reviews, 1 bedroom, 1.5 bathrooms
21–26 Aug
Guest favourite
Home in Leeward Settlement
Erisa Studio - Cozy Comfortf - 5 min to GraceBay
4.94 out of 5 average rating, 107 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Guest favourite
Villa in Long Bay Beach
Beach Bungalow Steps from Ocean!
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
7–12 Sept
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.89 out of 5 average rating, 28 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4.83 out of 5 average rating, 6 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Aug
Guest favourite
Place to stay in Providenciales
Cozy room/pool in Leeward near sunset, gracebay
4.96 out of 5 average rating, 51 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Leeward Settlement
"The Nest Cozy Cottage"
4.98 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug