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Search results; Over 1,000 homes in Leeward Settlement

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Guest favourite
Guest house in Leeward Settlement
Pelican Cottage -Mins. to the Beach!
Studio, 1 private bathroom
19–24 Sept
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4.91 out of 5 average rating, 158 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
16–21 Sept
4.91 out of 5 average rating, 58 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
28 Sept – 3 Oct
4.9 out of 5 average rating, 31 reviews
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Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 14 reviews
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Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Sept
4.61 out of 5 average rating, 18 reviews
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Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 34 reviews
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Luxe
Villa in Leeward Settlement
*Brand-new* Villa Terra Blue - Walk to Beach
4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 21 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
Villa in Leeward Settlement
*NEW* Villa Serenity - UESE 5
4 bedrooms, 4 beds, 3 bathrooms
17–22 Sept
4.94 out of 5 average rating, 17 reviews
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Villa in Leeward Settlement
Piccolo Ponte | 3 BR Canal Front | Pool & Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
New place to stay
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Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
16–21 Sept
4.86 out of 5 average rating, 7 reviews
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Luxe
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
17–22 Sept
5.0 out of 5 average rating, 4 reviews
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Luxe
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
16–21 Sept
4.91 out of 5 average rating, 33 reviews
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Villa in Leeward Settlement
Private Waterfront Lifestyle Villa -Turks & Caicos
4 bedrooms, 4 king beds, 4.5 bathrooms
17–22 Sept
4.92 out of 5 average rating, 66 reviews
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Guest favourite
Villa in Leeward Settlement
Waterfront Luxury Villa with Pool, Dock, Kayaks
5 bedrooms, 6 beds, 5.5 bathrooms
16–21 Sept
4.96 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 46 reviews