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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest house in Leeward Settlement
Pelican Cottage -Mins. to the Beach!
Studio, 1 private bathroom
1–6 Jul
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4.91 out of 5 average rating, 158 reviews
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
12–17 Jul
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
4.92 out of 5 average rating, 128 reviews, 3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.96 out of 5 average rating, 23 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
4.84 out of 5 average rating, 32 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Jul
Top guest favourite
Home in Grace Bay
#10 The Enclave
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
21–26 Sept
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
4.81 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
4.94 out of 5 average rating, 87 reviews, 2 bedrooms, 5 beds, 2 bathrooms
4–9 Jul
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
17–22 Aug
Guest favourite
Place to stay in Leeward Settlement
Minutes from Grace Bay Two
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, Toilet with sink
13–18 Jul
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
4.96 out of 5 average rating, 77 reviews, 1 bedroom, 1.5 bathrooms
31 Aug – 5 Sept
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
4.9 out of 5 average rating, 148 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
4.91 out of 5 average rating, 67 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, No bathroom
3–8 Jul
Guest favourite
Home in Leeward Settlement
Erisa Studio - Cozy Comfortf - 5 min to GraceBay
4.95 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Top guest favourite
Apartment in Providenciales
★★★★★ Modern Condo | Amazing Pool | On Site Spa
4.92 out of 5 average rating, 269 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Guest suite in Leeward Settlement
The Sandbox (UNIT 1)
4.99 out of 5 average rating, 94 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Villa in Long Bay Hills
Oceanfront Turquoise Dream Villa
4.87 out of 5 average rating, 70 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul