Windward holiday lettings
We found 2,351 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Windward by choosing from 99 houses, 36 apartments and other holiday rentals. Holiday homes provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Find spaces that suit your style
Find properties near top attractions in Windward
Map Attractions
Find the best place to stay - Windward
Modern 2 bedroom Villa, private heated pool, Couple & family friendly
Sleeps 5 · 2 bedrooms · 2 bathrooms
Top rated rentals - Windward
Photo gallery for BLUE LINE C OPEN VIEW ON THE OCEAN FACING THE WELL VENTILATED TURTLE ISLAND
Wonderful Stay
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Choose a holiday rental for your Windward getaway
Learn about the unique charm of Windward with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.
Exploring the natural features in Windward
Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Windward is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:
- Lorient Beach (0.7 mi / 1.2 km)
- Saline Beach (0.9 mi / 1.5 km)
- St. Jean Beach (1.6 mi / 2.6 km)
- Flamands Beach (3.2 mi / 5.1 km)
- Colombier Beach (3.8 mi / 6.1 km)
- Dawn Beach (16.8 mi / 27 km)