Windward holiday rentals

We found 32 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Windward to find one that's perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

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

Frequently asked questions

Are there holiday rentals in Windward?
Yes, there are holiday rentals close to the most popular sights in Windward, or you can select a more secluded option if you're looking for a relaxing stay.
What can I see and do in Windward?
While exploring the area, visit family-friendly sights like K1 Speed, or get outside and enjoy nature at Hollywood Beach. While in the area, you can also visit popular places such as Hard Rock Stadium and Seminole Hard Rock Casino Hollywood.
What are holiday rentals like in Windward?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windward. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.