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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Home in Leeward Settlement
PERIWINKLE | Charming Island Home|Near to Beach
2 bedrooms, 2 beds, 2 private bathrooms
3–8 Jul
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4.96 out of 5 average rating, 96 reviews
Top guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
28 Jul – 2 Aug
4.92 out of 5 average rating, 126 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
4.96 out of 5 average rating, 23 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
19–24 Jun
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Villa in Leeward
Butler Service, Waterfront Pickleball Villa
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 9 reviews
Home in Leeward Settlement
Blue Diamond Villa
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jun
4.8 out of 5 average rating, 5 reviews
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
24–29 Jun
4.94 out of 5 average rating, 87 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
4.91 out of 5 average rating, 67 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
7–12 Jul
4.95 out of 5 average rating, 20 reviews
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
19–24 Jun
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Long Bay Hills
LUXURy Villa: Ocean View. Private Pool! Chef avail
4 bedrooms, 5 beds, 4.5 bathrooms
7–12 Aug
4.92 out of 5 average rating, 78 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
20–25 Jun
Top guest favourite
Villa in The Bight Settlement
New private villa |Pool |300yds to Grace Bay beach
2 bedrooms, 2 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Discovery Bay
Luz Maria Villa- 3 bed 3 bath, Pool and Hot Tub!
3 bedrooms, 3 beds, 3 bathrooms
19–24 Jun
5.0 out of 5 average rating, 8 reviews
Villa in Leeward Settlement
Barefoot Bliss private pool & short walk to beach
2 bedrooms, 2 beds, 2 bathrooms
21–26 Jun