Holiday rentals in Leeward Settlement
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Top-rated holiday rentals in Leeward Settlement
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement holiday rentals
Other great holiday rentals in Leeward Settlement
Guest favourite
Home in Leeward Settlement
5.0 out of 5 average rating, 24 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
8–15 Sep
$1,034 SGD per night
Guest favourite
Villa in Caicos Islands
5.0 out of 5 average rating, 45 reviewsNEW Luxe Private Pool Villa, Golf Course View, BBQ
1–8 Aug
$702 SGD per night
Guest favourite
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
29 Jul – 5 Aug
$1,266 SGD per night
Guest favourite
Home in Leeward Settlement
4.98 out of 5 average rating, 49 reviewsCocodemer, a short walk to secluded Pelican Beach.
9–16 Mar
$516 SGD per night
Superhost
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
30 Sep – 7 Oct
$1,269 SGD per night
Superhost
Guest suite in Leeward Settlement
4.91 out of 5 average rating, 89 reviewsHandfield's Hideaway Cozy One Bedrm
7–14 Jun
$209 SGD per night
Guest favourite
Villa in Caicos Islands
4.94 out of 5 average rating, 87 reviewsCheers 🥂 Villa 🌴
18–25 Jul
$774 SGD per night
Guest favourite
Villa in Leeward Settlement
5.0 out of 5 average rating, 29 reviewsPerroquet | Family Villa near Leeward Beach
11–18 Oct
$826 SGD per night
Quick stats about holiday rentals in Leeward Settlement
Total rentals
290 properties
Rentals with a pool
240 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
5.2K reviews
Nightly prices starting at
$150 SGD before taxes and fees
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Holiday rentals
- Taylor Bay Holiday rentals
- North Caicos Holiday rentals
- Long Bay Beach Holiday rentals
- Sapodilla Bay Holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Salt Cay Holiday rentals
- Santiago de los Caballeros Holiday rentals
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Family-friendly rentals Leeward Settlement
- Beachfront rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a firepit Leeward Settlement
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- Monthly Rentals Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
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- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Villa rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
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