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51+ Osceola Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Osceola

Discover more than 51 holiday rentals in Osceola. Rent By Owner holiday homes has everything you need to find a place to stay near Osceola, MO.

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

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Frequently Asked Questions About Osceola Holiday Rentals

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

There are many holiday rentals available in Osceola; however, here are a few of the most popular holiday homes listed in Osceola 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 Osceola to find one that works for you.
Yes, there are 51 self-catering family homes and holiday rentals in Osceola.
There are more than 51 luxury holiday homes in or near Osceola, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: