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Search results; Over 1,000 homes in Leeward Settlement

Superhost
Holiday home in Leeward Settlement
The Caicos House
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
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Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
11–16 Sept
4.91 out of 5 average rating, 57 reviews
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
12–17 Sept
4.92 out of 5 average rating, 132 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Villa in Leeward Settlement
Leeward Jewel Villa - Luxurious 7 bedroom Canal Fr
7 bedrooms, 8 beds, 7 bathrooms
10–15 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.96 out of 5 average rating, 23 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
5–10 Sept
4.61 out of 5 average rating, 18 reviews
Villa in Leeward Settlement
Private Waterfront Lifestyle Villa -Turks & Caicos
4 bedrooms, 4 king beds, 4.5 bathrooms
6–11 Sept
4.92 out of 5 average rating, 66 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
12–17 Sept
4.9 out of 5 average rating, 30 reviews
Luxe
Villa in Leeward Settlement
*Brand-new* Villa Terra Blue - Walk to Beach
4 bedrooms, 5 beds, 4.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Leeward Settlement
Ocean Pearl Villa
3 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Sept
4.91 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
14–19 Sept
5.0 out of 5 average rating, 19 reviews
Superhost
Home in Caicos Islands
Harbour House - 3 Bed Waterfront; 7 Min to Beach
3 bedrooms, 4 beds, 3.5 bathrooms
6–11 Sept
4.91 out of 5 average rating, 34 reviews
Luxe
Villa in Leeward Settlement
Canalfront Turks & Caicos Villa w/ Infinity Pool
5 bedrooms, 7 beds, 5 bathrooms
5–10 Sept