38+ Jacob's Vineyard & Winery Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Jacob's Vineyard & Winery

Discover more than 38 holiday rentals in Jacob's Vineyard & Winery. Casai holiday homes have everything you need to find a place to stay near Jacob's Vineyard & Winery, MO.

Whether you are looking for luxury villas in Jacob's Vineyard & Winery, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartments for family holidays, or stylish accommodations 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 Jacob's Vineyard & Winery with a whole family or group, Casai holiday accommodations will make your trip memorable. We have plenty of places to stay in Jacob's Vineyard & Winery for families, large parties, or private owner accommodations for long or short trips. Jacob's Vineyard & Winery Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Jacob's Vineyard & Winery with Casai. Casai makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Jacob's Vineyard & Winery Holiday Rentals

There are a lot of options in Jacob's Vineyard & Winery. If you plan on staying in the Jacob's Vineyard & 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 Jacob's Vineyard & Winery:

There are many holiday rentals available in Jacob's Vineyard & Winery; however, here are a few of the most popular holiday homes listed in Jacob's Vineyard & Winery on our website:
At Casai.com most of our places to stay are perfect for families. Check out the complete list of holiday homes in Jacob's Vineyard & Winery to find one that works for you.
Yes, there are 38 self-catering family homes and holiday rentals in Jacob's Vineyard & Winery.
There are more than 38 luxury holiday homes in or near Jacob's Vineyard & Winery, according to 2025 data from Casai.com. Consider these homes for your next holiday:
Yes, there are 38 pet friendly rentals that are available in Jacob's Vineyard & Winery.