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.
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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
Home in Leeward Settlement
4.95 out of 5 average rating, 19 reviewsNEW! Getaway 2 bed villa/pool, 10% june near Beach
Guest favourite
Guesthouse in Leeward Settlement
4.97 out of 5 average rating, 93 reviews"The Nest Cozy Cottage"
Guest favourite
Apartment in Leeward Settlement
4.94 out of 5 average rating, 17 reviewsBeautiful Loft newly renovated
Guest favourite
Condo in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsGrace’s Condo In Leeward Settlement
Guest favourite
Condo in Caicos Islands
5.0 out of 5 average rating, 24 reviewsLil Chill -A cozy 1-Bedroom Unit near the beach
Guest favourite
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
Superhost
Guest suite in Leeward Settlement
4.91 out of 5 average rating, 89 reviewsHandfield's Hideaway Cozy One Bedrm
Superhost
Home in Leeward Settlement
4.95 out of 5 average rating, 63 reviewsPERIWINKLE | Charming Island Home|Near to Beach
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
$166 AUD before taxes and fees
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Accommodation & holiday rentals
- Taylor Bay Holiday rentals
- North Caicos Accommodation & holiday rentals
- Long Bay Beach Accommodation & holiday rentals
- Sapodilla Bay Accommodation & holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Salt Cay Holiday rentals
- Santo Domingo Accommodation & holiday rentals
- Santiago de los Caballeros Holiday rentals
- Las Terrenas Accommodation & holiday rentals
- Beachfront rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Rentals with a patio Leeward Settlement
- Apartment rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Villa rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with pools Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- House rentals Leeward Settlement
- Monthly Rentals Leeward Settlement
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