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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 bed, 1 private bathroom
18–23 Sept
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4.89 out of 5 average rating, 156 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
4.92 out of 5 average rating, 132 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
2–7 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
12–17 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
2–7 Sept
4.86 out of 5 average rating, 7 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
2–7 Sept
4.61 out of 5 average rating, 18 reviews
Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
2–7 Sept
4.98 out of 5 average rating, 54 reviews
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
1 bedroom, 1.5 bathrooms
3–8 Sept
4.96 out of 5 average rating, 84 reviews
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Sept
4.82 out of 5 average rating, 28 reviews
Guest favourite
Guest house in Long bay
Villa Kendara~50% 9/26-10/3 ~Beach~Privt~Gate~View
2 bedrooms, 4 beds, 1 bathroom
26 Sept – 2 Oct
4.94 out of 5 average rating, 97 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 89 reviews
Guest favourite
Home in Grace Bay
Gabriella Luxury Villa - Opening Special Rates
3 bedrooms, 3 beds, 4.5 bathrooms
3–8 Sept
4.95 out of 5 average rating, 19 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
2–7 Sept
4.84 out of 5 average rating, 32 reviews
Guest favourite
Place to stay in Providenciales
Cozy room/pool in Leeward near sunset, gracebay
1 bedroom, 1 queen bed, 1 bathroom
2–7 Sept
4.96 out of 5 average rating, 52 reviews