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
Apartment in Leeward Settlement
5.0 out of 5 average rating, 21 reviewsGrace’s Condo In Leeward Settlement
2–9 Nov
£271 per night
Guest favourite
Home in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
22–29 Oct
£863 per night
Superhost
Home in Leeward Settlement
4.95 out of 5 average rating, 60 reviewsPERIWINKLE | Charming Island Home|Near to Beach
26 Jun – 3 Jul
£262 per night
Guest favourite
Home in Leeward Settlement
4.98 out of 5 average rating, 50 reviewsCocodemer, a short walk to secluded Pelican Beach.
24–31 Oct
£326 per night
Guest favourite
Home in Providenciales
5.0 out of 5 average rating, 16 reviewsVilla Rae House in Long Bay Hills~walk to beach
7–14 Oct
£185 per night
Guest favourite
Villa in Caicos Islands
5.0 out of 5 average rating, 46 reviewsNEW Luxe Private Pool Villa, Golf Course View, BBQ
5–12 Nov
£440 per night
Guest favourite
Guest suite in Leeward Settlement
5.0 out of 5 average rating, 24 reviewsThe Sandbox (UNIT 1)
17–24 Jul
£166 per night
Guest favourite
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
27 Jul – 3 Aug
£790 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
£88 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
- Beachfront rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with a firepit Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Family-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
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- 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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