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  5. Holiday Homes

24+ Winter Haven Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Winter Haven

Discover more than 24 holiday rentals in Winter Haven. Rent By Owner holiday homes has everything you need to find a place to stay near Winter Haven, TX.

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

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Frequently Asked Questions About Winter Haven Holiday Rentals

There are a lot of options in Winter Haven. If you plan on staying in the Winter Haven 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 Winter Haven:

There are many holiday rentals available in Winter Haven; however, here are a few of the most popular holiday homes listed in Winter Haven 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 Winter Haven to find one that works for you.
Yes, there are 24 self-catering family homes and holiday rentals in Winter Haven.
There are more than 24 luxury holiday homes in or near Winter Haven, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: