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 Jul
,
4.91 out of 5 average rating, 158 reviews
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
6–11 Jul
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
3–8 Jul
4.98 out of 5 average rating, 52 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
4.9 out of 5 average rating, 51 reviews
Guest favourite
Villa in Leeward Settlement
Canal Front Villa - Private Dock & Pool BBQ
8 bedrooms, 9 beds, 7.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
4.96 out of 5 average rating, 23 reviews
Guest favourite
Villa in Providenciales
Salt Air Villa - Canalfront, Leeward
4 bedrooms, 5 beds, 4.5 bathrooms
25–30 Aug
4.77 out of 5 average rating, 35 reviews
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
5 bedrooms, 7 beds, 3.5 bathrooms
3–8 Jul
4.98 out of 5 average rating, 65 reviews
Villa in Leeward Settlement
Aqua Divina Villas
5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Jul
4.67 out of 5 average rating, 12 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 4 reviews
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
4.92 out of 5 average rating, 127 reviews
Villa in Providenciales
Salt Air and Second Wind
7 bedrooms, 8 beds, 7.5 bathrooms
25–30 Aug
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
4–9 Jul
5.0 out of 5 average rating, 45 reviews