South Portland Vacation Rentals

Our Favorite Vacation Rentals in South Portland

  • Crow's Nest
     Home/Apartment
    Booking.com
    From
    $306
  • WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $1,048
  • Turner Apartments
     Country House
    Booking.com
    From
    $99
  • Luxurious, Fully Renovated house with Private Beach rights.
     5br Home/Apartment
    HolidayLettings
    From
    $1,201
  • Cottage by the Sea
     Country House
    Booking.com
    From
    $170
  • Charming Downtown 1BR w/ Parking, Short Walk to Old Port
     Home/Apartment
    HolidayLettings
    From
    $356
  • Scouten Beachfront
     Country House
    Booking.com
    From
    $125
  • Higgins Beach Maine
    Excellent4br Cottage
    HolidayLettings
    From
    $406

Check prices for these upcoming dates

South Portland Vacation Rentals with a Pool

  • Loft Apartment on Tree-Lined Street in Falmouth
    ExcellentHome/Apartment
    Airbnb
    From
    $163

South Portland Vacation Rentals with Wi-Fi

  • Portland's Best Old Port & Beaches
    Excellent3br Home/Apartment
    Airbnb
    From
    $325
  • Cape Cottage Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $215
  • Explore Portland from a Historic Downtown Home
    Excellent2br Home/Apartment
    Airbnb
    From
    $225
  • CHEERFUL EAST END APARTMENT
    ExcellentHome/Apartment
    Airbnb
    From
    $131

South Portland Pet-Friendly Vacation Rentals

  • Portland Area Cottage w/OCEAN VIEWS ~ pet friendly
     3br Home/Apartment
    HolidayLettings
    From
    $998
  • Sleek condo w/ private patio - less than 2 blocks to beach/park, small dogs OK!
     2br Home/Apartment
    HolidayLettings
    From
    $245
  • The BumbleBee Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $127
  • Relaxing West End 2bd/1ba private unit
    Good2br Home/Apartment
    Airbnb
    From
    $112

South Portland Travel Guide

South Portland is a city in Cumberland County, Maine. The area has a long history as it was one of the first places reached by European and settlers in the 17th century. It's best known for its proximity to sandy beaches, water sports, and history.

Things to Do in South Portland

There are plenty of things to see and do in South Portland. Some of the top activities include exploring some of Maine's many nearby beaches, with the best in the area being the Spring Point Shoreway where you can find nice walking trails and an excellent view of the Casco Bay. Willard Beach is another top spot that's known for its white sand, long shores, and amenities. It's a great place to kick back and unwind with friends or family.

South Portland offers a variety of boat cruises, water sports, and fishing charters. If you always wanted to try paddle boarding or want to go lobster catching, this is the perfect place to do so. There are also boat tours where visitors can learn about the history of Maine and check out the heritage sites from the water.

Meanwhile, if you want to visit one of the most famous points of South Portland, head to the Spring Point Ledge Lighthouse, where you can visit the historic Fort Pebble. Here you can attend heritage and history tours to find out more about the area and the fort's history.

Best Places to Stay in South Portland

The best area to stay in South Portland is in Ferry Village where all the best bars, cafes, restaurants and clubs are located. There are parks and beaches in this area too, so everything will be right on your doorstep. There's a large selection of vacation rentals including cabins, beach cottages, luxury condos or big houses where you can enjoy a great stay with family or friends.

Best Time to Visit South Portland

Since South Portland is a coastal town the temperature is a little cooler than on the mainland where the ocean wind does not affect the weather. The best time to visit is in July when the weather is the warmest, and there is less rain than during the rest of the year.

Price and Availability in South Portland

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in South Portland tends to be Thursday, while the most expensive day tends to be Friday. Vacation homes in South Portland tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in South Portland is in January, while the cheapest month is in April. The most popular time to book a vacation rental in South Portland is in the high season in July. South Portland has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in South Portland

Rainy days
61°
10
55°
4
50° -17°
3
68°
4
58°
3
67° 23°
6
90° 33°
1
91° 46°
3
93° 51°
4
93° 53°
4
92° 41°
6
84° 25°
5
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in South Portland. The warmest months in South Portland are May and June, when temperatures reach 93 ˚F. The coolest month is December, when temperatures drop to -17 ˚F. The wettest month in South Portland is February with 10.26 inches of rain, while the driest month is August with 0.79 inches of rain.

What Expert Travelers Think

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    Whitney Wear
    Whitney WearTravel Better Guide
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

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Vacation Rentals in South Portland

Browse vacation rentals from all the best providers including Airbnb, Priceline, RedAwning and others at AllTheRooms.com. We have 373 vacation rentals, hotels and other accommodation types in South Portland ranging from inexpensive options to extravagant places to stay. A trip to South Portland can be affordable - our cheapest price accommodation is available at $20 a night. An average accommodation in South Portland costs on average $201 a night.

Those needing to get some work finished during their trip to South Portland can choose from 191 places to stay that have WiFi. We have 36 accommodations that come with breakfast included. You can keep up with your workout regime by staying at one of 11 accommodations that provide gym facilities. Driving to South Portland? Then choose one of the 187 places to stay that comes with a parking spot included. 8 accommodations come with a pool or jacuzzi

If you're traveling with your best friend, then be sure to select one of the 65 pet-friendly accommodations available.

In South Portland AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 3 providers, including 172 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from RedAwning.

227 accommodations in South Portland have been reviewed; 79% are rated excellent or good. 91 accommodations allow instant booking.

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