We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

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

$1,416 SGD for 5 nights

,

4.91 out of 5 average rating, 158 reviews

Top guest favourite

Villa in Leeward Settlement

Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks

5 bedrooms, 5 beds

13–18 Jul

$10,347 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Guest favourite

Villa in Leeward Settlement

Providenciales Beach Front Villa by Shoreline

3 bedrooms, 3 beds

15–20 Aug

$12,952 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 127 reviews

Guest favourite

Home in Leeward Settlement

Upper East Side Estates Gated Community Leeward

4 bedrooms, 4 beds

12–17 Jul

4.9 out of 5 average rating, 51 reviews

Top guest favourite

Villa in Leeward Settlement

Luxe Villa-Pool, Putting Green, Bocce, Near Beach

4 bedrooms, 4 beds

1–6 Aug

$9,330 SGD for 5 nights

4.96 out of 5 average rating, 23 reviews

Guest favourite

Villa in Long Bay Hills

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

3 bedrooms, 4 beds

14–19 Jul

$6,349 SGD for 5 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Leeward Settlement

Blue Tang Villa (2 Bedroom)

2 bedrooms, 2 beds

11–16 Aug

$5,507 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Guest favourite

Villa in Leeward Settlement

Caribbean Luxury Waterfront Villa w Housekeeping

3 bedrooms, 3 beds

27 Mar – 1 Apr

$11,923 SGD for 5 nights

5.0 out of 5 average rating, 36 reviews

Top guest favourite

Home in Grace Bay

Follow Your Dreams Villa!

2 bedrooms, 2 queen beds

17–22 Aug

$3,319 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 11 reviews

Guest favourite

Villa in Leeward Settlement

Villa Solymar Waterfront 4bedroom Villa with Pool

4 bedrooms, 5 beds

27 Jul – 1 Aug

$9,699 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Superhost

Villa in Leeward Settlement

Waterfront 5BR Villa - Kayak Sups Dock + Pool

5 bedrooms, 6 beds

12–17 Jul

$10,608 SGD for 5 nights

Top guest favourite

Home in Leeward Settlement

Vision Balance - Canal Front Home in Leeward

3 bedrooms, 6 beds

4–9 Jul

$7,980 SGD for 5 nights

5.0 out of 5 average rating, 45 reviews

Superhost

Home in Long Bay

Turkcation Villa with Curated Tropical Living

4 bedrooms, 5 beds

26–31 Jul

$7,821 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Townhouse in Grace Bay

Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay

4 bedrooms, 4 beds

1–6 Jul

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

20–25 Jul

$7,103 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews

Guest favourite

Villa in Grace Bay

Grace House Amazing home in the heart of Grace Bay

2 bedrooms, 2 king beds

1–6 Jul

$4,073 SGD for 5 nights

4.89 out of 5 average rating, 18 reviews

Guest favourite

Home in Leeward Settlement

Vacay Vibez Villa Luxury Water Front with Pool

3 bedrooms, 4 beds

7–12 Jul

$8,489 SGD for 5 nights

4.91 out of 5 average rating, 23 reviews

Guest favourite

Home in Leeward Settlement

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

2 bedrooms, 5 beds

4–9 Jul

$1,975 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 87 reviews

Superhost

Home in Leeward Settlement

Blue Tang Villa (5 Bedroom Main House)

5 bedrooms, 6 beds

23–28 Aug

$13,001 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews