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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Guest house in Leeward Settlement
"The Nest Cozy Cottage"
1 bedroom, 1 bed, 1 private bathroom
11–16 Aug
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4.98 out of 5 average rating, 131 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, 55 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, 33 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
12–17 Aug
New place to stay
Guest favourite
Villa in Grace Bay
Endless Honeymoon Villa
1 bedroom, 1.5 bathrooms
11–16 Aug
4.92 out of 5 average rating, 75 reviews
Top guest favourite
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 9 reviews
Villa in Long Bay Hills
Oceanfront Turquoise Dream Villa
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 73 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
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 17 reviews
Luxe
Home in Grace Bay
Villa Katava - 3BDR/3.5BATH on Grace Bay
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
11–16 Aug
4.61 out of 5 average rating, 18 reviews
Guest favourite
Home in Providenciales
2 Bedroom Stunning Views
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
11–16 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Providenciales
Private Luxury Villa with Pool 5 Min to GB Beach
1 bedroom, 1 bed, 1.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 382 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
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
11–16 Aug
4.97 out of 5 average rating, 34 reviews