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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Flat in Leeward Settlement
Romantic Apartment few steps from beach
1 bedroom, 1 bed, 1 private bathroom
8–13 Aug
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4.96 out of 5 average rating, 267 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
4.92 out of 5 average rating, 130 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
16–21 Aug
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 32 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
4.89 out of 5 average rating, 28 reviews
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 39 reviews
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Villa in The Bight Settlement
NEW Luxury Grace Bay villa|Pool | 2 min>Beach|Reef
2 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Providenciales
NEW Water Access! Luxe Villa, Infinity Pool& Views
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.91 out of 5 average rating, 53 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 88 reviews
Guest favourite
Villa in Grace Bay
Endless Honeymoon Villa
1 bedroom, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 75 reviews
Guest favourite
Home in Providenciales
2 Bedroom Spectacular Views
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Grace Bay
#10 The Enclave
2 bedrooms, 3 beds, 2.5 bathrooms
9–14 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Guest house in Providenciales
Oceanside Turtle Cove Cottage
1 bedroom, 1 bed, 1 bathroom
8–13 Aug
4.85 out of 5 average rating, 60 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
8–13 Aug
4.97 out of 5 average rating, 34 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
4.89 out of 5 average rating, 153 reviews
Top guest favourite
Villa in The Bight Settlement
Ideal private getaway villa | 250 yds to the beach
1 bedroom, 1 king bed, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 150 reviews