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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
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
4.92 out of 5 average rating, 128 reviews, 3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4.9 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
4.94 out of 5 average rating, 87 reviews, 2 bedrooms, 5 beds, 2 bathrooms
4–9 Jul
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.96 out of 5 average rating, 23 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
27 Jul – 1 Aug
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Leeward Settlement
Blue Tang Villa (2 Bedroom)
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 2 bathrooms
11–16 Aug
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.89 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
17–22 Aug
Superhost
Home in 144645
Villa Starfish
4.76 out of 5 average rating, 17 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
12–17 Jul
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
4.91 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
7–12 Jul
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 6 beds, 2 bathrooms
4–9 Jul
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
4.96 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
Top guest favourite
Villa in Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
6–11 Jul