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Search results; Over 1,000 places in Leeward Settlement

Superhost
Home in Leeward Settlement
💦 LIQUID 💦 LUXURY Villa 🖤 on the WATER !!!💙
5 beds
6–11 Apr
$1,666 SGD per night, originally $1,814 SGD
4.91 out of 5 average rating, 88 reviews
Guest favourite
Apartment in Leeward Settlement
New! Luxury 1Bed Large Condo
1 bed
19–24 Apr
$480 SGD per night
4.95 out of 5 average rating, 37 reviews
Guest favourite
Villa in Long Bay Hills
VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
2 beds
12–17 May
$775 SGD per night
4.97 out of 5 average rating, 79 reviews
Guest favourite
Villa in Leeward Settlement
Unique, Modern Cozy & Private | 2 minutes to Beach
2 king beds
20–25 Apr
$895 SGD per night
4.98 out of 5 average rating, 52 reviews
Guest favourite
Home in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 beds
17–22 May
$1,210 SGD per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Villa in Leeward Settlement
Byculla Villa
4 king beds
9–14 Apr
$1,847 SGD per night, originally $2,309 SGD
5.0 out of 5 average rating, 32 reviews
Superhost
Villa in Leeward Settlement
YOLO - Never second guess a vacation worth taking
6 beds
30 Apr – 5 May
$1,276 SGD per night
Home in Caicos Islands
! ! NEW ! ! Designers Dream Marina's Beach House
7 beds
9–14 Apr
$1,221 SGD per night, originally $1,569 SGD
4.83 out of 5 average rating, 12 reviews
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
7 beds
19–24 Mar
$2,008 SGD per night, originally $2,543 SGD
5.0 out of 5 average rating, 39 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa
3 beds
14–19 Apr
$1,738 SGD per night
4.92 out of 5 average rating, 53 reviews
Guest favourite
Villa in Grace Bay
Calico Villa
3 beds
8–13 Jun
$1,396 SGD per night
4.96 out of 5 average rating, 85 reviews
Villa in Leeward Settlement
Live style villa
4 beds
6–11 Apr
$2,022 SGD per night
Superhost
Villa in Long Bay
Villa Julia
6 beds
7–12 Apr
$3,202 SGD per night, originally $4,002 SGD
New place to stay
Superhost
Home in Leeward Settlement
Bellagio Blu - 4 Bedrooms
4 beds
2–7 Apr
$1,606 SGD per night
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Caicos Islands
Legacy Palms Villa
5 beds
14–19 Apr
$1,567 SGD per night, originally $1,712 SGD
4.9 out of 5 average rating, 69 reviews
Guest favourite
Home in Providenciales
Villa Flamenco - Luxury Vacation Home
4 beds
15–20 Apr
$2,017 SGD per night
4.93 out of 5 average rating, 14 reviews
Villa in Leeward Settlement
Caribbean Escape Luxe Waterfront Villa with Pool
9 beds
15–20 Apr
$5,388 SGD per night, originally $6,560 SGD
New place to stay
Superhost
Villa in Caicos Islands
Villa Seadream - Upper East Side Enclave #16
4 king beds
1–6 May
$1,540 SGD per night, originally $1,925 SGD
5.0 out of 5 average rating, 3 reviews