1. USA
  2. Florida
  3. Sumter County
  4. Holiday Homes

1976+ Sumter County Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Sumter County

Discover more than 1976 holiday rentals in Sumter County. PickleTrip™ holiday homes has everything you need to find a place to stay near Sumter County, FL.

Whether you are looking for luxury villas in Sumter County, 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 with private pickleball courts or nearby facilities. 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 Sumter County with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Sumter County for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Sumter County with PickleTrip™. Stay and play pickleball when you travel.

Show more
Show less

Frequently Asked Questions About Sumter County Holiday Rentals

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

There are many holiday rentals available in Sumter County; however, here are a few of the most popular holiday homes listed in Sumter County on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Sumter County to find one that works for you.
Yes, there are 1976 self-catering family homes and holiday rentals in Sumter County.
There are more than 1976 luxury holiday homes in or near Sumter County, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 1976 pet friendly rentals that are available in Sumter County.