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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 bed, 1 private bathroom
18–23 Sept
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4.89 out of 5 average rating, 156 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds
2–7 Sept
4.89 out of 5 average rating, 38 reviews
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds
2–7 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds
2–7 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Villa in Leeward Settlement
Waterfront Luxury Villa with Pool, Dock, Kayaks
5 bedrooms, 6 beds
2–7 Sept
4.96 out of 5 average rating, 24 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
7–12 Sept
4.92 out of 5 average rating, 132 reviews
Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds
2–7 Sept
4.97 out of 5 average rating, 30 reviews
Luxe
Villa in Leeward Settlement
*Brand-new* Villa Terra Blue - Walk to Beach
4 bedrooms, 5 beds
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds
2–7 Sept
4.61 out of 5 average rating, 18 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds
8–13 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds
2–7 Sept
4.86 out of 5 average rating, 7 reviews
Guest favourite
Villa in Caicos Islands
Modern 4BR oasis on 1 acre, 1 min from the Beach
4 bedrooms, 5 beds
2–7 Sept
4.92 out of 5 average rating, 111 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds
12–17 Sept
4.9 out of 5 average rating, 30 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds
8–13 Sept
4.96 out of 5 average rating, 23 reviews
Superhost
Home in Leeward Settlement
Casa Verde - 7BR on the Canal across from Beach
7 bedrooms, 8 beds
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Caicos Islands
Harbour House - 3 Bed Waterfront; 7 Min to Beach
3 bedrooms, 4 beds
3–8 Sept
4.91 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
1–6 Oct
5.0 out of 5 average rating, 34 reviews
Luxe
Villa in Leeward Settlement
Sunset Bay Villa - 10 mins away from Grace Bay
5 bedrooms, 5 beds
4–9 Sept
5.0 out of 5 average rating, 5 reviews