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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest house in Leeward Settlement
Pelican Cottage -Mins. to the Beach!
Studio, 1 private bathroom
6–11 Sept
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4.91 out of 5 average rating, 158 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
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
3–8 Sept
4.97 out of 5 average rating, 35 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, 156 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
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
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
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
3–8 Sept
4.86 out of 5 average rating, 7 reviews
Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms, 2 beds, 2 bathrooms
3–8 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
3–8 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
3–8 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.98 out of 5 average rating, 42 reviews
Guest favourite
Flat in Leeward Settlement
Luxury Paradise 1 Bedroom condo+pool in Grace Bay
1 bedroom, 1 king bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 94 reviews
Guest favourite
Villa in Long Bay Hills
Private Romantic Beachfront Getaway!
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 7 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
Guest favourite
Flat in Grace Bay
Palms Hideaway II....7 mins to Grace Bay Beach!!
1 bedroom, 1 bed, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 83 reviews
Guest favourite
Home in Providenciales
2 Bedroom Spectacular Views
2 bedrooms, 2 beds, 2 bathrooms
3–8 Sept
5.0 out of 5 average rating, 48 reviews