96+ Portland Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Portland

Discover more than 96 holiday rentals in Portland. Casai holiday homes have everything you need to find a place to stay near Portland, CT.

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

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Frequently Asked Questions About Portland Holiday Rentals

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

There are many holiday rentals available in Portland; however, here are a few of the most popular holiday homes listed in Portland on our website:
At Casai.co.za most of our places to stay are perfect for families. Check out the complete list of holiday homes in Portland to find one that works for you.
Yes, there are 96 self-catering family homes and holiday rentals in Portland.
There are more than 96 luxury holiday homes in or near Portland, according to 2025 data from Casai.co.za. Consider these homes for your next holiday:
Yes, there are 96 pet friendly rentals that are available in Portland.