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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 private bathrooms
1–6 Sept
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4.9 out of 5 average rating, 71 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
4.92 out of 5 average rating, 130 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
16–21 Aug
4.91 out of 5 average rating, 55 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 33 reviews
Superhost
Home in Grace Bay
Live Villa - 2 BDR in Grace Bay
2 bedrooms, 2 beds, 2.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Aug
4.97 out of 5 average rating, 34 reviews
Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Villa in Leeward Settlement
Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
13–18 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
12–17 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds, 3 bathrooms
12–17 Aug
4.89 out of 5 average rating, 38 reviews
Guest favourite
Villa in Leeward Settlement
Luxury Canal Front Villa Kayaks, Pool & BBQ
8 bedrooms, 9 beds, 7.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Providenciales
NEW - Aqua Blu Beachfront Villa "The Palm"
4 bedrooms, 4 king beds, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
4.89 out of 5 average rating, 28 reviews
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
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