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Search results; Over 1,000 homes in Leeward Settlement

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Top guest favourite
Guest house in Leeward Settlement
Private 1BR Cottage | 100 Steps to Beach | Rooftop
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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4.98 out of 5 average rating, 132 reviews
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Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
1–6 Oct
4.91 out of 5 average rating, 58 reviews
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Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
13–18 Oct
4.92 out of 5 average rating, 132 reviews
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Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
18–23 Oct
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Oct
4.97 out of 5 average rating, 35 reviews
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Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds, 2 bathrooms
3–8 Oct
4.71 out of 5 average rating, 108 reviews
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Guest favourite
Guest house in Long bay
Villa Kendara~SALE~OCT 3-10~Beach~Privt~Gated~View
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 98 reviews
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Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Oct
4.61 out of 5 average rating, 18 reviews
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Home in Leeward Settlement
Luxe 1BR Canal Suite w/ Pool • Near Grace Bay
1 bedroom, 1 queen bed, 1 bathroom
9–14 Oct
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Top guest favourite
Holiday home in Venetian Road Settlement
Lovely studio apartment, with pool
1 bedroom, 1 bed, 1 bathroom
15–20 Oct
4.95 out of 5 average rating, 99 reviews
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Top guest favourite
Guest suite in Leeward Settlement
The Sandbox (UNIT 1)
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
4.99 out of 5 average rating, 99 reviews
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Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Oct
4.9 out of 5 average rating, 31 reviews
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Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
28 Oct – 2 Nov
4.89 out of 5 average rating, 159 reviews
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Guest favourite
Villa in Leeward Settlement
Luxury Canal Front Villa Kayaks, Pool & BBQ
8 bedrooms, 9 beds, 7.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 9 reviews
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Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Oct
4.83 out of 5 average rating, 30 reviews
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Guest favourite
Flat in Leeward Settlement
Luxury Paradise 1 Bedroom condo+pool in Grace Bay
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 95 reviews
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Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
31 Oct – 5 Nov
4.96 out of 5 average rating, 23 reviews
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Superhost
Home in Grace Bay
25% Off September! Walk To Beach W/Private Pool
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
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