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Search results; Over 1,000 homes in Leeward Settlement

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Top guest favourite
Flat in Leeward Settlement
Romantic Apartment few steps from beach
1 bedroom, 1 bed, 1 private bathroom
12–17 Nov
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4.96 out of 5 average rating, 269 reviews
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Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
13–18 Oct
4.92 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
1–6 Oct
4.91 out of 5 average rating, 58 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
3–8 Oct
4.94 out of 5 average rating, 98 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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Villa in Leeward Settlement
Piccolo Ponte | 3 BR Canal Front | Pool & Hot Tub
3 bedrooms, 3 beds
1–6 Oct
New place to stay
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Guest favourite
Villa in Caicos Islands
Sunlit Waterfront Villa w/Pool, Dock, Near Beaches
4 bedrooms, 5 beds
6–11 Oct
4.94 out of 5 average rating, 33 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, 159 reviews
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Top guest favourite
Home in Leeward Settlement
Ocean Pearl Villa
3 bedrooms, 6 beds
3–8 Oct
5.0 out of 5 average rating, 13 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, 19 reviews
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Superhost
Home in Leeward Settlement
Villa Enandi
5 bedrooms, 6 beds
12–17 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds
1–6 Oct
4.86 out of 5 average rating, 7 reviews
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Villa in Leeward Settlement
Private Waterfront Lifestyle Villa -Turks & Caicos
4 bedrooms, 4 king beds
1–6 Oct
4.92 out of 5 average rating, 66 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
Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds
1–6 Oct
4.97 out of 5 average rating, 30 reviews
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Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds
3–8 Oct
4.71 out of 5 average rating, 108 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