Photo by Staci Partlo
Leeward Settlement holiday rentals
We found 1,100 holiday rentals — enter your dates for availability
Discover a selection of 60 homes, 162 villas and holiday rentals in Leeward Settlement that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the amenities that you expect and more, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Leeward Settlement
30 Seconds to the Grace Bay Beach! 5 BR, Private Pool, Lush Gardens!!!
Sleeps 13 · 5 bedrooms · 3 bathrooms
10 out of 10
exceptional
(33 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Book a holiday rental for your Leeward Settlement getaway
Learn about the unique charm of Leeward Settlement with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.
Exploring the natural features in Leeward Settlement
Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Leeward Settlement. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:
- Leeward Beach (1 mi / 1.6 km)
- Long Bay Beach (1.1 mi / 1.8 km)
- Grace Bay Beach (2.6 mi / 4.2 km)
- Providenciales Beaches (4.7 mi / 7.6 km)
- Pelican Beach (5.6 mi / 8.9 km)
- Sapodilla Bay (10.1 mi / 16.3 km)
Transport options to and around Leeward Settlement
Fly into Providenciales (PLS-Providenciales Intl.), the closest airport, located 8.3 mi (13.4 km) from the city centre.