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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest house in Leeward Settlement
Pelican Cottage -Mins. to the Beach!
Studio, 1 private bathroom
1–6 Aug
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4.91 out of 5 average rating, 158 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
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, 31 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, 54 reviews
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
New place to stay
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 32 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
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 25 reviews
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
11–16 Aug
4.95 out of 5 average rating, 22 reviews
Home in Providenciales
NEW - Aqua Blu Beachfront Villa "The Palm"
4 bedrooms, 4 king beds, 5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
3 bedrooms, 4 beds, 3.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 12 reviews
Home in Leeward Settlement
Beach Cottage
1 bedroom, 1 bed, 1 bathroom
2–9 Sept
New place to stay
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
3–8 Aug
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 38 reviews
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Aug
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Home in Grace Bay
Hopewell Villa East/Pool & walk to Gracebay Beach
2 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
4.97 out of 5 average rating, 72 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
18–23 Aug
4.98 out of 5 average rating, 53 reviews