132+ Whitefish Bay Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Whitefish Bay

Discover more than 132 holiday rentals in Whitefish Bay. PickleTrip™ holiday homes has everything you need to find a place to stay near Whitefish Bay, WI.

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

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Frequently Asked Questions About Whitefish Bay Holiday Rentals

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

There are many holiday rentals available in Whitefish Bay; however, here are a few of the most popular holiday homes listed in Whitefish Bay on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Whitefish Bay to find one that works for you.
Yes, there are 132 self-catering family homes and holiday rentals in Whitefish Bay.
There are more than 132 luxury holiday homes in or near Whitefish Bay, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 132 pet friendly rentals that are available in Whitefish Bay.