113+ The Cloisters Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near The Cloisters

Discover more than 113 holiday rentals in The Cloisters. Rent By Owner holiday homes has everything you need to find a place to stay near The Cloisters, FL.

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

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Frequently Asked Questions About The Cloisters Holiday Rentals

There are a lot of options in The Cloisters. If you plan on staying in the The Cloisters 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 The Cloisters:

There are many holiday rentals available in The Cloisters; however, here are a few of the most popular holiday homes listed in The Cloisters 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 The Cloisters to find one that works for you.
Yes, there are 113 self-catering family homes and holiday rentals in The Cloisters.
There are more than 113 luxury holiday homes in or near The Cloisters, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: