Windward holiday rentals

We found 2,628 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Windward by choosing from 96 houses, 42 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.

Popular Windward destinations on Stayz

Morne Criquet

Morne Criquet

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More 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)
  • Gouverneur Beach (1.4 mi / 2.3 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)

Frequently asked questions

What is the most popular type of holiday home accommodation in Windward?
Villas are the most popular kind of holiday home in Windward, according to our data. Even if you’ve got something bigger or smaller in mind, Stayz has properties in loads of sizes and shapes. Look through our options to find your ideal fit.
How much does it cost to rent a holiday home in Windward?
Several factors can determine what you’ll pay for a holiday home in Windward, like the season, length of stay and type of property. However, all our holiday homes have something in common — incredible value. Simply add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Windward?
Prices for beach houses in Windward may differ depending on the type and size of the property and when you’re travelling. Just enter your travel dates into Stayz and the number of guests to see available options and prices. From there you can use our filter tool to refine your search by ratings, amenities, nearby activities and more.
What are popular home amenities in Windward?
The most popular home amenities people look for in Windward include a microwave oven, a fridge and a private pool. Whether you’re on a trip with friends, family or even pets, Stayz holiday properties have the best amenities for beginning new traditions with the people who matter most.
Are there large group holiday homes in Windward?
With 188 holiday homes that can sleep 10 people or more in Windward, there’s no need to hold back on your invites. From family get-togethers to events like Christmas or New Year’s Eve parties, Stayz will help you find a large group home to match the occasion.
Can I find two-bedroom holiday homes in Windward?
Windward has 399 two-bedroom holiday homes for you to select from. Enjoy a holiday home with all the privacy and comfort you’re looking for at an attractive price on Stayz.
Are there holiday homes with WiFi in Windward?
Windward has 340 holiday homes with WiFi, so you can stay connected while you’re on holiday. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with the family to posting pics on social media, these Stayz homes make it easy to go online.
How old do you have to be to rent a holiday home in Windward?
Age restrictions can differ across properties on Stayz, so look at the rules of the holiday home in Windward you want. But in general, it’s 16, 18 or 21.
How long can I rent a holiday home in Windward for?
It’s up to the Windward property. To view a list of options offering extended stays, just enter your dates and number of guests into the Stayz search page. You can enjoy having the property to yourself, along with home comforts such as a kitchen, air conditioning and a yard where your little ones can play. Keep an eye out for any long-term stays that offer weekly or monthly discounts.

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