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752+ Windley Key Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windley Key

Discover more than 752 holiday rentals in Windley Key. Rent By Owner holiday homes has everything you need to find a place to stay near Windley Key, FL.

Whether you are looking for luxury villas in Windley Key, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Windley Key with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Windley Key for families, large parties, or private owner accommodations for long or short trips. Windley Key Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Windley Key with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Windley Key Holiday Rentals

There are a lot of options in Windley Key. If you plan on staying in the Windley Key area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Windley Key:

There are many holiday rentals available in Windley Key; however, here are a few of the most popular holiday homes listed in Windley Key on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Windley Key to find one that works for you.
Yes, there are 752 self-catering family homes and holiday rentals in Windley Key.
There are more than 752 luxury holiday homes in or near Windley Key, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: