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.
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
Condo in Leeward Settlement
5.0 out of 5 average rating, 21 reviewsGrace’s Condo In Leeward Settlement
Nov. 2 – 9
Home in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
Oct. 22 – 29
Home in Leeward Settlement
4.95 out of 5 average rating, 60 reviewsPERIWINKLE | Charming Island Home|Near to Beach
Jun. 26 – Jul. 3
Home in Leeward Settlement
4.98 out of 5 average rating, 50 reviewsCocodemer, a short walk to secluded Pelican Beach.
Oct. 24 – 31
Home in Providenciales
5.0 out of 5 average rating, 16 reviewsVilla Rae House in Long Bay Hills~walk to beach
Oct. 7 – 14
Villa in Caicos Islands
5.0 out of 5 average rating, 46 reviewsNEW Luxe Private Pool Villa, Golf Course View, BBQ
Nov. 5 – 12
Guest suite in Leeward Settlement
5.0 out of 5 average rating, 24 reviewsThe Sandbox (UNIT 1)
Jul. 17 – 24
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
Jul. 27 – Aug. 3
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
$150 CAD before taxes and fees
Destinations to explore
- Grace Bay Vacation rentals
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- Beachfront rentals Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Rentals with a firepit Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Monthly Rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with beach access Leeward Settlement
- House rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Villa rentals Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
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