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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
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Guest favourite
Apartment in Caicos Islands
4.97 out of 5 average rating, 30 reviewsLil Chill -A cozy 1-Bedroom Unit near the beach
![](https://a0.muscache.com/im/pictures/miso/Hosting-49985048/original/13a008f3-d6c9-4907-ad84-049328c50074.jpeg?im_w=720)
Guest favourite
Villa in Leeward Settlement
4.89 out of 5 average rating, 44 reviewsSea Sun Relax - villa 5 min walk to Grace Bay
![](https://a0.muscache.com/im/pictures/bb926102-4a5f-4e43-87cc-139b79142209.jpg?im_w=720)
Guest favourite
Guest suite in Leeward Settlement
4.94 out of 5 average rating, 72 reviewsErisa Studio near Grace Bay Beach
![](https://a0.muscache.com/im/pictures/miso/Hosting-890518679885443271/original/6d250080-81cc-41fb-86f8-15dd6b550548.jpeg?im_w=720)
Guest favourite
Home in Grace Bay
5 out of 5 average rating, 19 reviewsVilla in Providenciales
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-597694892118960991/original/558df952-ba67-433e-b3ae-97ddd25f86d3.jpeg?im_w=720)
Guest favourite
Villa in Caicos Islands
4.95 out of 5 average rating, 55 reviewsLuxe Private Pool Villa, Golf Course View, BBQ
![](https://a0.muscache.com/im/pictures/miso/Hosting-1026834773515146097/original/8d6d1847-370b-4e6e-9f4f-e9dd9a1c352b.jpeg?im_w=720)
Guest favourite
Rental unit in Leeward Settlement
4.95 out of 5 average rating, 22 reviewsBeautiful Loft newly renovated
![](https://a0.muscache.com/im/pictures/05bd5e0a-12cb-4dbb-be96-98c9526521df.jpg?im_w=720)
Guest favourite
Villa in Leeward Settlement
5 out of 5 average rating, 31 reviewsPerroquet | Family Villa near Leeward Beach
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-47172333/original/e9deb6c4-68df-40bc-b85f-1ddf8bfa18d1.jpeg?im_w=720)
Superhost
Villa in Providenciales, Long Bay Beach
5 out of 5 average rating, 16 reviewsPrivate Villa w Pool and Hotel Amenities/Services
Quick stats about holiday rentals in Leeward Settlement
Total rentals
310 properties
Nightly prices starting at
€ 101 before taxes and fees
Total number of reviews
5.8K reviews
Family-friendly rentals
240 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
260 properties have a pool
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
- Santo Domingo Holiday rentals
- Santiago de los Caballeros Holiday rentals
- Las Terrenas Holiday rentals
- Rentals with a hot tub Leeward Settlement
- Beachfront rentals Leeward Settlement
- Rentals with a patio Leeward Settlement
- Luxury rentals Leeward Settlement
- Flat rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a firepit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Villa rentals Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Family-friendly rentals Leeward Settlement
- House rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with pools Leeward Settlement
- Monthly Rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
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