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Homes in Leeward Settlement
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Search results; Over 1,000 homes in Leeward Settlement
Over 1,000 homes in Leeward Settlement
Top guest favourite
Guest favourite
Guest house in Leeward Settlement
"The Nest Cozy Cottage"
1 bedroom
,
·
1 bed
,
·
1 private bathroom
12–17 Jul
12–17 Jul
$2,312 SGD
$2,135 SGD
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for 5 nights
,
·
4.98 out of 5 average rating, 130 reviews
4.98 (130)
Top guest favourite
Guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
4 bathrooms
4 bathrooms
13–18 Jul
13–18 Jul
$10,239 SGD
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for 5 nights
$10,239 SGD for 5 nights
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favourite
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
12–17 Jul
12–17 Jul
$8,602 SGD
$7,310 SGD
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for 5 nights
4.9 out of 5 average rating, 52 reviews
4.9 (52)
Top guest favourite
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4.5 bathrooms
4.5 bathrooms
14–19 Aug
14–19 Aug
$9,290 SGD
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for 5 nights
$9,290 SGD for 5 nights
4.96 out of 5 average rating, 24 reviews
4.96 (24)
Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$2,893 SGD
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for 5 nights
$2,893 SGD for 5 nights
Guest favourite
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
19–24 Jul
19–24 Jul
$4,288 SGD
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for 5 nights
$4,288 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
27 Aug – 1 Sept
27 Aug – 1 Sept
$6,616 SGD
$6,085 SGD
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for 5 nights
Extended stay discount
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Superhost
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
5.5 bathrooms
5.5 bathrooms
23–28 Aug
23–28 Aug
$11,688 SGD
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for 5 nights
$11,688 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
No bathroom
No bathroom
18–23 Aug
18–23 Aug
$6,395 SGD
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for 5 nights
$6,395 SGD for 5 nights
4.98 out of 5 average rating, 53 reviews
4.98 (53)
Top guest favourite
Guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
26–31 Aug
26–31 Aug
$4,377 SGD
$3,731 SGD
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for 5 nights
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Guest favourite
Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
20–25 Jul
20–25 Jul
$8,653 SGD
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for 5 nights
$8,653 SGD for 5 nights
4.89 out of 5 average rating, 37 reviews
4.89 (37)
Luxe
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms
9 bedrooms
,
·
9 beds
9 beds
,
·
9.5 bathrooms
9.5 bathrooms
16–21 Jul
16–21 Jul
$54,822 SGD
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for 5 nights
$54,822 SGD for 5 nights
Superhost
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
13–18 Jul
13–18 Jul
$10,562 SGD
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for 5 nights
$10,562 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Superhost
Superhost
Home in Long Bay Hills
LUXURy Villa: Ocean View. Private Pool! Chef avail
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4.5 bathrooms
4.5 bathrooms
17–22 Aug
17–22 Aug
$5,445 SGD
$4,544 SGD
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for 5 nights
4.92 out of 5 average rating, 79 reviews
4.92 (79)
Guest favourite
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4.5 bathrooms
4.5 bathrooms
2–7 Aug
2–7 Aug
$9,657 SGD
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for 5 nights
$9,657 SGD for 5 nights
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Villa in Leeward Settlement
Villa Cariad
4 bedrooms
4 bedrooms
,
·
4 king beds
4 king beds
,
·
5 bathrooms
5 bathrooms
28 Jul – 2 Aug
28 Jul – 2 Aug
$7,429 SGD
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for 5 nights
$7,429 SGD for 5 nights
Guest favourite
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,929 SGD
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for 5 nights
$2,929 SGD for 5 nights
4.9 out of 5 average rating, 69 reviews
4.9 (69)
Top guest favourite
Guest favourite
Villa in Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
16–21 Aug
16–21 Aug
$11,055 SGD
$9,580 SGD
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for 5 nights
Book early to save
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Superhost
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$5,142 SGD
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for 5 nights
$5,142 SGD for 5 nights
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