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 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
4.92 out of 5 average rating, 127 reviews
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
4.96 out of 5 average rating, 23 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Jul
4.84 out of 5 average rating, 32 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Caicos Islands
Guest Apartment near Grace Bay Beach
1 bedroom, 3 beds, 1 bathroom
7–12 Jul
4.97 out of 5 average rating, 103 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
4.91 out of 5 average rating, 67 reviews
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
1 bedroom, 1.5 bathrooms
1–6 Jul
4.96 out of 5 average rating, 77 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
7–12 Jul
4.95 out of 5 average rating, 20 reviews
Villa in Long Bay Hills
Oceanfront Turquoise Dream Villa
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.87 out of 5 average rating, 70 reviews
Top guest favourite
Villa in Leeward
Butler Service, Waterfront Pickleball Villa
4 bedrooms, 7 beds, 3.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Grace Bay
#10 The Enclave
2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Aug
4.96 out of 5 average rating, 26 reviews
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 29 reviews
Superhost
Villa in Long Bay
Hakuna Matata Villa
3 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
4.87 out of 5 average rating, 75 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
3–8 Jul
4.98 out of 5 average rating, 52 reviews