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, 127 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
Home in Leeward Settlement
Blue Diamond Villa
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Jul
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Villa in Leeward
Butler Service, Waterfront Pickleball Villa
4 bedrooms, 7 beds, 3.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
4 bedrooms, 5 beds, 3 bathrooms
20–25 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Leeward Settlement
Blue Tang Villa (2 Bedroom)
2 bedrooms, 2 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
3 bedrooms, 4 beds, 3.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
4–9 Jul
5.0 out of 5 average rating, 45 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
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Jul
New place to stay
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
12–17 Jul
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 10 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
Flat in Leeward Settlement
Villa 714 mar
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
New place to stay
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
6–11 Jul