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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Guest house in Leeward Settlement
"The Nest Cozy Cottage"
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.98 out of 5 average rating, 130 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
12–17 Jul
4.92 out of 5 average rating, 129 reviews
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, 30 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, 52 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, 24 reviews
Flat in The Bight Settlement
The Penthouse Apartment With Ocean Views
2 bedrooms, 2 beds, 2 bathrooms
7–12 Jul
New place to stay
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Home in Providenciales
NEW -Aqua Blu Beach Villa 1-Oceanfront Paradise
4 bedrooms, 4 king beds, 4.5 bathrooms
13–18 Jul
New place to stay
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
7–12 Jul
4.95 out of 5 average rating, 20 reviews
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Villa in Caicos Islands
Modern Canal Front Villa in Leeward
3 bedrooms, 3 king beds, 4 bathrooms
20–25 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Villa in Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
4 bedrooms, 7 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 17 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
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 30 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
7–12 Jul