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Search results; Over 1,000 homes in Leeward Settlement

Superhost
Guest house in Leeward Settlement
Lois Estates: 2 Bed Unique Home - Long Bay
2 bedrooms, 1 bed, 2.5 private bathrooms
1–6 Sept
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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
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, 29 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
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 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
1–6 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
15–20 Sept
4.86 out of 5 average rating, 7 reviews
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.61 out of 5 average rating, 18 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
4.89 out of 5 average rating, 155 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.96 out of 5 average rating, 23 reviews
Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.89 out of 5 average rating, 38 reviews
Flat in Long Bay Hills
3-bedrooms Suite Next to Grace Bay
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.8 out of 5 average rating, 25 reviews
Guest favourite
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Grace Bay
Boutique Villa w Private Beach Chairs on Grace Bay
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 55 reviews
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Sept
4.82 out of 5 average rating, 28 reviews
Guest favourite
Villa in Leeward Settlement
3BR Villa | Pool | 100 Steps to Pelican Beach
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.75 out of 5 average rating, 61 reviews