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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite

Guest house in Leeward Settlement

"The Nest Cozy Cottage"

1 bedroom, 1 bed, 1 private bathroom

14–19 Jul

$2,084 SGD for 5 nights

,

4.98 out of 5 average rating, 130 reviews

Top guest favourite

Villa in Leeward Settlement

Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks

5 bedrooms, 5 beds, 4 bathrooms

14–19 Jul

$10,259 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

16–21 Aug

4.9 out of 5 average rating, 52 reviews

Top guest favourite

Villa in Leeward Settlement

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

4 bedrooms, 4 beds, 4.5 bathrooms

14–19 Aug

$9,308 SGD for 5 nights

4.96 out of 5 average rating, 24 reviews

Home in Long Bay Hills

Twins Villa - Mellizo B

2 bedrooms, 2 beds, 2 bathrooms

14–19 Jul

Guest favourite

Home in Leeward Settlement

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

2 bedrooms, 5 beds, 2 bathrooms

28 Jul – 3 Aug

$2,738 SGD for 6 nights

4.94 out of 5 average rating, 88 reviews

Guest favourite

Home in Leeward Settlement

Caicos Cove Villa Private Pool, BBQ near Grace Bay

4 bedrooms, 5 beds, 3 bathrooms

27 Aug – 1 Sept

Extended stay discount

4.95 out of 5 average rating, 21 reviews

Luxe

Villa in Providenciales

Villa Khaya - Bespoke Waterfront Home

4 bedrooms, 4 beds, 4 bathrooms

2–7 Aug

$8,557 SGD for 5 nights

4.9 out of 5 average rating, 10 reviews

Superhost

Villa in Leeward Settlement

Waterfront 5BR Villa - Kayak Sups Dock + Pool

5 bedrooms, 6 beds, 4 bathrooms

5–10 Aug

$10,583 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Villa in Long Bay Hills

3 Bedrooms Villa Near The Beach

3 bedrooms, 5 beds, 3 bathrooms

26–31 Aug

4.97 out of 5 average rating, 36 reviews

Top guest favourite

Villa in Leeward

Luxury Waterfront Villa | Dock, Pool & Pickleball

4 bedrooms, 7 beds, 3.5 bathrooms

16–21 Aug

Book early to save

5.0 out of 5 average rating, 10 reviews

Guest favourite

Villa in Leeward Settlement

Villa Solymar Waterfront 4bedroom Villa with Pool

4 bedrooms, 5 beds, 4.5 bathrooms

2–7 Aug

$9,676 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Superhost

Villa in The Bight Settlement

Turquoise Coral Villa 2 BDR Grace Bay beach

2 bedrooms, 2 king beds, 2 bathrooms

7–12 Nov

$6,638 SGD for 5 nights

4.88 out of 5 average rating, 17 reviews

Top guest favourite

Home in Leeward Settlement

PERIWINKLE | Charming Island Home|Near to Beach

2 bedrooms, 2 beds, 2 bathrooms

14–19 Jul

$2,718 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

Villa in Leeward Settlement

Villa Cariad

4 bedrooms, 4 king beds, 5 bathrooms

28 Jul – 2 Aug

$7,444 SGD for 5 nights

Luxe

Home in Leeward Settlement

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

9 bedrooms, 9 beds, 9.5 bathrooms

16–21 Jul

$54,931 SGD for 5 nights

Top guest favourite

Villa in The Bight Settlement

New private villa |Pool |300yds to Grace Bay beach

2 bedrooms, 2 beds, 2 bathrooms

4–9 Aug

$4,803 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews

Superhost

Home in Leeward Settlement

Blue Tang Villa (5 Bedroom Main House)

5 bedrooms, 6 beds, 5.5 bathrooms

23–28 Aug

$11,711 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Villa in Providenciales

Blue Flamingo Villa - Paradise Is a Lifestyle!

3 bedrooms, 4 beds, 2.5 bathrooms

19–24 Jul

$4,297 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews