108+ Greenwood Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Greenwood

Discover more than 108 holiday rentals in Greenwood. PickleTrip™ holiday homes has everything you need to find a place to stay near Greenwood, MS.

Whether you are looking for luxury villas in Greenwood, 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 Greenwood with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Greenwood 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 Greenwood with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Greenwood Holiday Rentals

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

There are many holiday rentals available in Greenwood; however, here are a few of the most popular holiday homes listed in Greenwood on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Greenwood to find one that works for you.
Yes, there are 108 self-catering family homes and holiday rentals in Greenwood.
There are more than 108 luxury holiday homes in or near Greenwood, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 108 pet friendly rentals that are available in Greenwood.