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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
25–30 Jul
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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
4.92 out of 5 average rating, 130 reviews, 3 bedrooms, 3 beds, 3 bathrooms
18–23 Jul
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4.9 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.9 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Top guest favourite
Villa in Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Aug
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.92 out of 5 average rating, 26 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 5 beds, 3 bathrooms
11–16 Aug
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 31 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Villa in Leeward Settlement
Live style villa
4.89 out of 5 average rating, 37 reviews, 4 bedrooms, 4 beds, 3 bathrooms
20–25 Jul
Superhost
Villa in Providenciales
Cascade Villa lll- Modern 1BR/1BR Mins to Gracebay
New place to stay, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Jul
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Villa in Venetian Road Settlement
French Cay Estate on Turtle Lake
5.0 out of 5 average rating, 68 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
4.94 out of 5 average rating, 88 reviews, 2 bedrooms, 5 beds, 2 bathrooms
28 Jul – 3 Aug
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
4.99 out of 5 average rating, 67 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
18–23 Jul
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
18–23 Jul