Portland Vacation Rentals

Compare 616 vacation rentals with savings up to 30% off this summer.
USA > Maine > Portland

Make Portland your next getaway

Experience a bustling working waterfront, one of the nation's most exciting culinary epicenters, and easy access to the year-round beauties of Midcoast Maine by booking a getaway to one of our charming Portland vacation rentals! Founded by Great Britain as a trade and fishing settlement in 1632, Portland has seen its turn as a trade power, a shipping mecca, and the largest city in Maine, which today is home to nearly one-quarter of the state population in the city's greater metropolitan area.

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Condo rentals

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House rentals

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Portland vacation rentals for every getaway

Dog-friendly Hot tub Internet
Cumberland Casa - A
2 Bed | 1 Bath | Sleeps 6

Cumberland Casa - A - Portland, ME

$285 avg / night
East End Annex
1 Bed | 1 Bath | Sleeps 2

East End Annex - Portland, ME

$257 avg / night
Historic Hideaway, Apt #4
1 Bed | 1 Bath | Sleeps 2

Historic Hideaway, Apt #4 - Portland, ME

$266 avg / night
Cumberland Charm
1 Bed | 1 Bath | Sleeps 4

Cumberland Charm - Portland, ME

$208 avg / night
The Heart of the West End #3
2 Bed | 2 Bath | Sleeps 4

The Heart of the West End #3 - Portland, ME

$411 avg / night

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Recent Portland vacation rental reviews

A great modern 2 bed 2 bath on the west side! The living space between the bedroom is great to separate the people staying in the apartment. Water pressure is great, apartment comes stocked with fundamentals (paper towels, dish detergent, etc). I would say that if you’re noise sensitive like me, bring earplugs for your sleep as you won’t know who is staying above you. You might be able to make out some laughs and conversations. You know a place is great when your dog approves and feels comfortable!
Yea Jin L. | May 2023
This place was perfect for a solo weekend getaway.
Elena M. | May 2023
This place was just perfect! Super clean and cozy! Perfect location. Walk to the waterfront for great restaurants and shops. Will definitely be back!!
Christine J. | May 2023
Portland Frequently Asked Questions

Yes, 15 of our Portland homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 57 of our Portland vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Portland vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Portland team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Portland, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Whether you're an outdoorsman, a food lover, a lighthouse enthusiast, or a foliage-watcher, you'll find the perfect home away from home in these Southern Maine vacation rentals.

Where is Portland, ME?

Originally called Machigonne - or "Great Neck" - by the Native Americans who first lived in the region, the city of Portland occupies a peninsula in Southern Maine's Casco Bay. Although this coastal city is in the far northeastern reaches of New England, it is also an easy and scenic drive just 112 miles south to Boston and 52 miles south to Portsmouth, NH. 

Things to Do in Portland, ME

Leveled by a great fire in 1866 and almost entirely rebuilt in the Victorian Era, Portland is a city of 19th century architecture and historic charm. And perhaps nowhere are Portland's past and present better displayed than the Old Port, a revitalized warehouse district that connects the working waterfront to an eclectic collection of shops and restaurants.

Looking to sample the bounty of a city built upon the fishing industry? Guests at our Portland vacation homes will find a rapidly growing culinary scene, where chefs showcase the very best local ingredients to attract diners from all over the country. Fill your days with pastries from Standard Baking Co. and classic lobster rolls from Fisherman's Grill; end your evenings with delectable small plates at Central Provisions, the freshest local oysters at Eventide Oyster Co., and farm-to-table splurges at the legendary Fore Street.

Thanks to its scenic coastal location, Portland is also an ideal place to explore the outdoor beauties of Maine. Drive five miles through South Portland to reach Cape Elizabeth and the Portland Head Light, which is believed to be the most photographed lighthouse in the world. You can also stop by Portland Paddle to rent stand-up paddle boards and book guided kayaking tours of Casco Bay.

Day Trips from Portland, ME

Whether you're planning a winter retreat, a summer beach vacation, or a search for New England's most glorious fall foliage, Portland is the perfect home base for excursions across coastal Maine.

In the warm summer months, head 28 miles south to Kennebunkport, the quaint community of beachgoers made famous by the Bush family compound.

A scenic drive east on Highway One will allow visitors to discover the picturesque towns, charming harbors, and pristine coastlines of Midcoast Maine. In search of history? Head 35 miles east to the Maine Maritime Museum, the renowned facility located between the shipbuilding city of Bath and its bucolic coastal neighbor, West Bath. Looking for lobster rolls? Join the summer crowds that rightfully line up outside Red's Eats in the waterfront town of Wiscasset. Yearning for natural beauty? Launch your kayak near Southport, Boothbay Harbor, or East Boothbay to explore the Sheepscot River, the Damariscotta River, or Damariscove Island just offshore.

Feel up to traveling a bit further? Spend the day 82 miles east of Portland in Camden Hills State Park, a collection of gorgeous hillside trails that overlook the serene Camden harbor. Just be sure to stop for dinner at Primo on the way home - this James Beard Award winner in the neighboring city of Rockland is one of the most beloved restaurants in Maine.

Experience the tastes, landscapes, and sights of New England as they were meant to be enjoyed - book one of our Portland vacation rentals today!