122+ Winthrop Beach Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Winthrop Beach

Discover more than 122 holiday rentals in Winthrop Beach. Casai holiday homes have everything you need to find a place to stay near Winthrop Beach, MA.

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

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Frequently Asked Questions About Winthrop Beach Holiday Rentals

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

There are many holiday rentals available in Winthrop Beach; however, here are a few of the most popular holiday homes listed in Winthrop Beach on our website:
At Casai.ca most of our places to stay are perfect for families. Check out the complete list of holiday homes in Winthrop Beach to find one that works for you.
Yes, there are 122 self-catering family homes and holiday rentals in Winthrop Beach.
There are more than 122 luxury holiday homes in or near Winthrop Beach, according to 2025 data from Casai.ca. Consider these homes for your next holiday:
Yes, there are 122 pet friendly rentals that are available in Winthrop Beach.