1. USA
  2. Wisconsin
  3. Enterprise
  4. Holiday Homes

169+ Enterprise Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Enterprise

Discover more than 169 holiday rentals in Enterprise. Rent By Owner holiday homes has everything you need to find a place to stay near Enterprise, WI.

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

Show more
Show less

Frequently Asked Questions About Enterprise Holiday Rentals

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

There are many holiday rentals available in Enterprise; however, here are a few of the most popular holiday homes listed in Enterprise 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 Enterprise to find one that works for you.
Yes, there are 169 self-catering family homes and holiday rentals in Enterprise.
There are more than 169 luxury holiday homes in or near Enterprise, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: