Vacation rentals in Leeward Settlement
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Top-rated vacation rentals in Leeward Settlement
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Leeward Settlement vacation rentals
Other great vacation rentals in Leeward Settlement
Guest favourite
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
Jul. 29 – Aug. 5
$1,339 CAD per night
Superhost
Guest suite in Leeward Settlement
4.91 out of 5 average rating, 89 reviewsHandfield's Hideaway Cozy One Bedrm
Jun. 7 – 14
$209 CAD 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
Jan. 13 – 20
$970 CAD per night
Guest favourite
Home in Leeward Settlement
4.95 out of 5 average rating, 60 reviewsPERIWINKLE | Charming Island Home|Near to Beach
Nov. 29 – Dec. 6
$467 CAD per night
Guest favourite
Villa in Caicos Islands
4.94 out of 5 average rating, 87 reviewsCheers 🥂 Villa 🌴
Jun. 28 – Jul. 5
$905 CAD per night
Superhost
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
Apr. 29 – May 6
$1,408 CAD per night
Guest favourite
Villa in Leeward Settlement
5.0 out of 5 average rating, 29 reviewsPerroquet | Family Villa near Leeward Beach
Aug. 29 – Sep. 5
$923 CAD per night
Guest favourite
Home in Providenciales
4.96 out of 5 average rating, 82 reviewsSunny Paradise Long Bay
Jan. 2 – 9
$671 CAD per night
Quick stats about vacation 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
$151 CAD before taxes and fees
Destinations to explore
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- Luxury rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
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- Rentals with a hot tub Leeward Settlement
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- Villa rentals Leeward Settlement
- Rentals with a firepit Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Rentals with a kayak Leeward Settlement
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