Portland Vacation Rentals

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USA > Maine > Portland

Make Portland your next getaway—choose from 8 great vacation rentals

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

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A Foodie’s Delight
1 Bed | 1 Bath | Sleeps 4

A Foodie’s Delight - Portland, ME

From $205
Cumberland Corner 3D Tour
3 Bed | 2 Bath | Sleeps 8 (6 Adults Max)

Cumberland Corner - Portland, ME

From $153
Back Cove Views 3D Tour
2 Bed | 1 Bath | Sleeps 6 (4 Adults Max)

Back Cove Views - Portland, ME

From $125
Cumberland Charm 3D Tour
1 Bed | 1 Bath | Sleeps 4

Cumberland Charm - Portland, ME

From $170
Waterfront View Escape 3D Tour
2 Bed | 1 Bath | Sleeps 4

Waterfront View Escape - Portland, ME

From $109

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Recent Portland vacation rental reviews

Great location, walking distance to downtown, but away from all the tourists, traffic, and parking headaches. Spotlessly clean and newly refurbished. A comfortable, quiet basement apartment with convenient off-street parking. Only downside was lack of a table, so although the kitchen is reasonably well-outfitted, there is no place to eat comfortably.
Laura G. | Sep 2021
nice place—new and attractive, comfortable bed, A/C worked well, ang great locationon the east end with lots of restaurants near by. Annoyances were: #1. an App-based tv. Difficult to use and the problems that can happen when you stream—frame freezes, dropouts, pixelization—can happen on any station. #2- when we arrived and saw a brand new kitchen, we said wow! however found that the ice maker and filtered water on the fridge didn’t work. Reported to the management company on the Wednesday we arrived—not resolved until Monday. #3 Safety issue: found that when you were reheating a cup of coffee and using the toaster oven at the same time, it popped the circuit breaker. dangerous and needs to addressed by an electrician.
Kristine S. | Sep 2021
First time visiting Portland, and Morning on the Atlantic was perfect stay for my husband and I. It was within walking distance to many places and as pictured. The bikes were a plus as we were able to ride around and enjoy the scenery. Hope one day we are able to return!
Abbey W. | Aug 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
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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!