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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
4.92 out of 5 average rating, 130 reviews, 3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4.91 out of 5 average rating, 53 reviews, 4 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
4.92 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
3–8 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
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.89 out of 5 average rating, 28 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4.83 out of 5 average rating, 6 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Aug
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Villa in Providenciales
NEW- Aqua Blu Beach Villa Oceanfront "The Jasmine"
New place to stay, 4 bedrooms, 4 beds, 4.5 bathrooms
7–12 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
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 32 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 6 beds, 4 bathrooms
5–10 Aug
Top guest favourite
Home in Grace Bay
Hopewell Villa East/Pool & walk to Gracebay Beach
4.97 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 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
1–6 Aug
Flat in Leeward Settlement
Marbella Suite 2 | Caribbean Elegance & Luxury
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, No bathroom
18–23 Aug
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
14–19 Aug