43+ St. James Winery Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near St. James Winery

Discover more than 43 holiday rentals in St. James Winery. PickleTrip™ holiday homes has everything you need to find a place to stay near St. James Winery, MO.

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

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Frequently Asked Questions About St. James Winery Holiday Rentals

There are a lot of options in St. James Winery. If you plan on staying in the St. James Winery 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 St. James Winery:

There are many holiday rentals available in St. James Winery; however, here are a few of the most popular holiday homes listed in St. James Winery on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in St. James Winery to find one that works for you.
Yes, there are 43 self-catering family homes and holiday rentals in St. James Winery.
There are more than 43 luxury holiday homes in or near St. James Winery, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 43 pet friendly rentals that are available in St. James Winery.