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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
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
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
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
25–30 Aug
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–18 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
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
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
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
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4.95 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 3 bathrooms
7–12 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
5–10 Jul
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
4.96 out of 5 average rating, 77 reviews, 1 bedroom, 1.5 bathrooms
4–9 Aug
Guest favourite
Flat in Leeward Settlement
15 mins walk to restaurants and beach
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Jul
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
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