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Search results; Over 1,000 homes in Leeward Settlement

Superhost
Holiday home in Leeward Settlement
The Caicos House
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
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Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
11–16 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
12–17 Sept
4.92 out of 5 average rating, 132 reviews
Villa in Leeward Settlement
Piccolo Ponte | 3 BR Canal Front | Pool & Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
New place to stay
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
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
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Sept
4.97 out of 5 average rating, 35 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
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.89 out of 5 average rating, 157 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
25 Sept – 1 Oct
4.94 out of 5 average rating, 97 reviews
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
14–19 Sept
4.83 out of 5 average rating, 30 reviews
Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.84 out of 5 average rating, 32 reviews
Guest favourite
Flat in Caicos Islands
Guest Apartment near Grace Bay Beach
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 107 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
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.71 out of 5 average rating, 107 reviews
Guest favourite
Villa in Leeward Settlement
3BR Villa | Pool | 100 Steps to Pelican Beach
3 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.75 out of 5 average rating, 61 reviews
Guest favourite
Home in Grace Bay
Gabriella Luxury Villa - Opening Special Rates
3 bedrooms, 3 beds, 4.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 19 reviews