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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

$1,413 SGD for 5 nights

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4.91 out of 5 average rating, 158 reviews

Guest favourite

Villa in Leeward Settlement

Providenciales Beach Front Villa by Shoreline

3 bedrooms, 3 beds, 3 bathrooms

15–20 Aug

$12,920 SGD for 5 nights

4.92 out of 5 average rating, 128 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

$10,440 SGD for 5 nights

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

Guest favourite

Home in Leeward Settlement

Guest House 2B&2B near Grace Bay Beach & Long Bay

2 bedrooms, 5 beds, 2 bathrooms

4–9 Jul

$1,970 SGD for 5 nights

4.94 out of 5 average rating, 87 reviews

Guest favourite

Villa in Providenciales

Blue Flamingo Villa - Paradise Is a Lifestyle!

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Jul

$4,580 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Villa in Long Bay Hills

Private Pool Villa w/ BBQ, & Fire Pit + Near Beach

3 bedrooms, 4 beds, 3.5 bathrooms

27 Jul – 1 Aug

$7,055 SGD for 5 nights

5.0 out of 5 average rating, 11 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

$9,307 SGD for 5 nights

4.96 out of 5 average rating, 23 reviews

Guest favourite

Home in Leeward Settlement

Caicos Cove Villa Private Pool, BBQ near Grace Bay

4 bedrooms, 5 beds, 3 bathrooms

7–12 Jul

Extended stay discount

4.95 out of 5 average rating, 20 reviews

Top guest favourite

Home in Leeward Settlement

Vision Balance - Canal Front Home in Leeward

3 bedrooms, 6 beds, 2 bathrooms

4–9 Jul

$7,960 SGD for 5 nights

5.0 out of 5 average rating, 45 reviews

Top guest favourite

Home in Grace Bay

Follow Your Dreams Villa!

2 bedrooms, 2 queen beds, 2.5 bathrooms

17–22 Aug

$3,349 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in Leeward Settlement

Blue Tang Villa (2 Bedroom)

2 bedrooms, 2 beds, 2 bathrooms

11–16 Aug

$5,493 SGD for 5 nights

5.0 out of 5 average rating, 15 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

Luxe

Villa in Providenciales

Villa Khaya - Bespoke Waterfront Home

4 bedrooms, 4 beds, 4 bathrooms

2–7 Aug

$8,555 SGD for 5 nights

4.89 out of 5 average rating, 9 reviews

Superhost

Home in Leeward Settlement

Beach Daze Villa - Your Tropical Vacation Awaits

3 bedrooms, 6 beds, 2 bathrooms

1–6 Jul

$5,151 SGD for 5 nights

Top guest favourite

Villa in Leeward

Luxury Waterfront Villa | Dock, Pool & Pickleball

4 bedrooms, 7 beds, 3.5 bathrooms

6–11 Jul

$8,890 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Superhost

Home in Leeward Settlement

Blue Tang Villa (5 Bedroom Main House)

5 bedrooms, 6 beds, 5.5 bathrooms

23–28 Aug

$11,709 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Leeward Settlement

Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ

3 bedrooms, 3 beds, 3.5 bathrooms

20–25 Jul

$7,085 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews

Top guest favourite

Villa in Venetian Road Settlement

French Cay Estate on Turtle Lake

5 bedrooms, 6 beds, 3 bathrooms

27 Jul – 1 Aug

5.0 out of 5 average rating, 66 reviews