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Search results; Over 1,000 homes in Leeward Settlement

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Top guest favourite
Villa in Leeward Settlement
Cocodemer, a short walk to secluded Pelican Beach.
2 bedrooms, 3 beds, 2 private bathrooms
14–19 Nov
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4.96 out of 5 average rating, 75 reviews
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Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds
1–6 Oct
4.92 out of 5 average rating, 60 reviews
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Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds
1–6 Oct
4.97 out of 5 average rating, 35 reviews
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Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds
18–23 Oct
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed
28 Oct – 2 Nov
4.89 out of 5 average rating, 160 reviews
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Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
23–28 Nov
4.92 out of 5 average rating, 133 reviews
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Top guest favourite
Holiday home in Venetian Road Settlement
Lovely studio apartment, with pool
1 bedroom, 1 bed
15–20 Oct
4.95 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
1–6 Oct
4.91 out of 5 average rating, 32 reviews
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Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds
1–6 Oct
4.61 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds
1–6 Oct
5.0 out of 5 average rating, 20 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
1–6 Oct
5.0 out of 5 average rating, 95 reviews
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Guest favourite
Villa in Leeward Settlement
*NEW* Villa Serenity - UESE 5
4 bedrooms, 4 beds
1–6 Oct
4.94 out of 5 average rating, 17 reviews
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Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds
1–6 Oct
4.89 out of 5 average rating, 38 reviews
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Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds
24–29 Oct
4.96 out of 5 average rating, 23 reviews
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Superhost
Guest house in Leeward Settlement
Pelican Cottage -Mins. to the Beach!
1–6 Oct
4.91 out of 5 average rating, 159 reviews
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Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 46 reviews
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Guest favourite
Villa in Leeward Settlement
Luxury Canal Front Villa Kayaks, Pool & BBQ
8 bedrooms, 9 beds
18–23 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Cottage in Providenciales
Hummingbird Guesthouse Sleeps 3 250m from beach
1 bedroom, 2 beds
18–23 Nov
4.86 out of 5 average rating, 49 reviews
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Top guest favourite
Guest suite in Leeward Settlement
The Sandbox (UNIT 1)
1 bedroom, 1 king bed
1–6 Oct
4.99 out of 5 average rating, 99 reviews