Holiday houses 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.
Holiday rentals for every style
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Popular amenities for Leeward Settlement holiday rentals
Other great holiday rentals in Leeward Settlement
Condo in Leeward Settlement
5.0 out of 5 average rating, 21 reviewsGrace’s Condo In Leeward Settlement
2 – 9 Nov
Home in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
22 – 29 Oct
Home in Leeward Settlement
4.95 out of 5 average rating, 60 reviewsPERIWINKLE | Charming Island Home|Near to Beach
26 June – 3 July
Home in Leeward Settlement
4.98 out of 5 average rating, 50 reviewsCocodemer, a short walk to secluded Pelican Beach.
24 – 31 Oct
Home in Providenciales
5.0 out of 5 average rating, 16 reviewsVilla Rae House in Long Bay Hills~walk to beach
7 – 14 Oct
Villa in Caicos Islands
5.0 out of 5 average rating, 46 reviewsNEW Luxe Private Pool Villa, Golf Course View, BBQ
5 – 12 Nov
Guest suite in Leeward Settlement
5.0 out of 5 average rating, 24 reviewsThe Sandbox (UNIT 1)
17 – 24 July
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
27 July – 3 Aug
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
$171 AUD 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
- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Beachfront rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Luxury rentals Leeward Settlement
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- Rentals with a fire pit Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- House rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Monthly Rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
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