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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest suite in Leeward Settlement
Handfield's Hideaway Cozy One Bedrm
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.92 out of 5 average rating, 102 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
Superhost
Home in Providenciales
Villa Mariposa Oceanfront Views Steps to the beach
3 bedrooms, 4 beds, 3 bathrooms
10–15 Sept
New place to stay
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
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
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
Live style villa
4 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
4.89 out of 5 average rating, 38 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
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
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 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
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
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
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
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
Luxe
Villa in Long Bay
Coco Rock - Villa Julia (Villa Julia)
5 bedrooms, 8 beds, 5.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 24 reviews