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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

$1,411 SGD for 5 nights

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4.91 out of 5 average rating, 158 reviews

Guest favourite

Villa in Leeward Settlement

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

3 bedrooms, 3 beds, No bathroom

3–8 Jul

$5,682 SGD for 5 nights

4.98 out of 5 average rating, 52 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

$10,427 SGD for 5 nights

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

1–6 Jul

$5,145 SGD for 5 nights

Villa in Leeward Settlement

Aqua Divina Villas

5 bedrooms, 8 beds, 5.5 bathrooms

1–6 Jul

$9,448 SGD for 5 nights

4.67 out of 5 average rating, 12 reviews

Luxe

Villa in Providenciales

Villa Khaya - Bespoke Waterfront Home

4 bedrooms, 4 beds, 4 bathrooms

2–7 Aug

$8,545 SGD for 5 nights

4.89 out of 5 average rating, 9 reviews

Guest favourite

Villa in Providenciales

Amazing Waterfront Villa on Leeward Canals

5 bedrooms, 7 beds, 3.5 bathrooms

3–8 Jul

$12,571 SGD for 5 nights

4.98 out of 5 average rating, 65 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

$9,295 SGD for 5 nights

4.96 out of 5 average rating, 23 reviews

Superhost

Home in Long Bay

Turkcation Villa with Curated Tropical Living

4 bedrooms, 5 beds, 3 bathrooms

26–31 Jul

$7,800 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Villa in Caicos Islands

Waterfront Villa &Pool - Cotton House-Sups -Kayak

4 bedrooms, 5 beds, 3 bathrooms

12–17 Jul

$8,888 SGD for 5 nights

5.0 out of 5 average rating, 8 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

Superhost

Villa in Providenciales

The Caicos House -5 mins to the Beach & Dining!

3 bedrooms, 5 beds, 2.5 bathrooms

1–6 Jul

$4,290 SGD for 5 nights

4.84 out of 5 average rating, 32 reviews

Guest favourite

Villa in Providenciales

Salt Air Villa - Canalfront, Leeward

4 bedrooms, 5 beds, 4.5 bathrooms

25–30 Aug

4.77 out of 5 average rating, 35 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

Home in Leeward Settlement

CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock

9 bedrooms, 9 beds, 9.5 bathrooms

6–11 Jul

$54,855 SGD for 5 nights

Guest favourite

Villa in Leeward Settlement

Providenciales Beach Front Villa by Shoreline

3 bedrooms, 3 beds, 3 bathrooms

15–20 Aug

$12,904 SGD for 5 nights

4.92 out of 5 average rating, 128 reviews

Top guest favourite

Home in Leeward Settlement

Vision Balance - Canal Front Home in Leeward

3 bedrooms, 6 beds, 2 bathrooms

4–9 Jul

$7,950 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

$3,345 SGD for 5 nights

5.0 out of 5 average rating, 12 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