Discover a selection of 500 vacation rentals in Portland that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $248 per night, and houses and cabins are popular options for a stay in Portland. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Portland
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Destination guide

Find style and sophistication with a Portland cabin rental

Portland cabins in Maine are in the center of a mixture of outdoor adventures and artistic endeavors. The region is stylish and sophisticated, boasting a trendy tech, fashion, and culinary scene, though the local atmosphere is still laid back and quiet. You’ll find plenty of fun things to do, ranging from excellent dining to adventures on the rocky shoreline.

 
History

Historic sites near vacation homes in Portland

Portland has a rich history that’s displayed through many heritage sites. Vacation rentals can be found near places like Victoria Mansion, a 19th-century Italian villa with an ornate interior and museum, and the Portland Observatory, a historic maritime signal tower and museum. You could also visit Bug Light, a historic lighthouse inspired by a Greek monument with spectacular harbor views.

Things to do

Sightseeing near Portland vacation rentals

Portland Head Light is one of the city’s most iconic landmarks. The 1791 lighthouse was the first to be built in the state of Maine, and still shines its beam over the entrance to Portland Harbor. Its fame was further enhanced when Edward Hopper made it the subject of one of his best-known paintings. The former lighthouse keeper’s cottage is now a museum, where you can learn more about the historic structure and how it has kept pace with technological changes. The complex is situated within Fort Williams Park, an military site that played a vital role during both World Wars.

Activities

Things to do near Portland vacation homes

A walking tour of the Old Port district is one of the highlights of any first-time visit to Portland. This quaint quarter of cobblestone streets and fishing piers was once the commercial hub of the Portland peninsula. The disused buildings were saved from demolition in the 1970s and converted into desirable living and working spaces. Today, the Old Port pulses with life day and night, with a wealth of restaurants and bars, fashion boutiques, street entertainment, and cultural events. The annual Old Port Festival is a red-letter day, offering family-friendly activities, local food specialties, and live music.

Weather

Local weather for your stay in Portland vacation homes

The climate of Portland falls within the range of humid continental, resulting in cold, snowy winters and warm, moderately wet summers. Thanks to its location on the Gulf of Maine, summer humidity is moderated by the cool waters of the Atlantic Ocean. In high summer, it’s a good idea to look for Portland vacation rentals with a pool or close to the beaches of Casco Bay, to provide welcome refreshment at the end of an action-packed day. A good tip for finding bargains in Portland vacation rentals is to visit during spring or fall, when temperatures are ideal for sightseeing.

Natural features

Marine life in Portland

Casco Bay’s fishing heritage lives on in its abundant marine life. Predominant species include mackerel, bluefish, and striped bass, along with crustaceans such as mussels, clams, and the tasty lobsters that are a specialty of Maine restaurants. Fishing trips can be booked within easy reach of downtown Portland vacation rentals, with the likelihood of bringing home a freshly caught supper. Native and migrating sea birds also benefit from the protective bay, most commonly cormorants, gulls, and ducks. Rare sightings of ospreys, eagles, and herons are a bonus for keen bird-watchers.

How to get there

Transportation options to and around Portland

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 2.6 mi (4.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Brunswick, ME (NHZ-Brunswick Executive), which is 23.2 mi (37.3 km) away.

If you'd rather travel by train, the main station serving the city is Portland Transportation Center.

Good for couples

Couple's retreat near Portland vacation homes

Portland’s scenery and quirky attractions set the perfect stage for a couple’s retreat. Vacation homes can be found near places like the Umbrella Cover Museum, a specialty museum with a whimsical collection of umbrella covers, and Commercial Street, a downtown area with unique shops and boutiques. You'll also like the Tate House Museum, a colonial-era home of a British naval officer with period furnishings and tours.

How many vacation rentals are available around Portland?

Our 2021 property listings offer a large selection of 661 vacation rentals around Portland. From 355 house rentals to 83 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Explore destinations around Portland

Downtown Portland
78 vacation rentals
West Bayside
79 vacation rentals
West End
57 vacation rentals
Back Cove
23 vacation rentals
Parkside
61 vacation rentals
Munjoy Hill
50 vacation rentals
East Bayside
61 vacation rentals
Rosemont
23 vacation rentals
East Deering
17 vacation rentals
Deering Center
19 vacation rentals
Oakdale
49 vacation rentals
Valley Street
52 vacation rentals