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272+ Oak Harbor Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Oak Harbor

Discover more than 272 holiday rentals in Oak Harbor. PickleTrip™ holiday homes has everything you need to find a place to stay near Oak Harbor, WA.

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

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Frequently Asked Questions About Oak Harbor Holiday Rentals

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

There are many holiday rentals available in Oak Harbor; however, here are a few of the most popular holiday homes listed in Oak Harbor on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Oak Harbor to find one that works for you.
Yes, there are 272 self-catering family homes and holiday rentals in Oak Harbor.
There are more than 272 luxury holiday homes in or near Oak Harbor, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 272 pet friendly rentals that are available in Oak Harbor.