South Portland Vacation Rentals

Our Favorite Vacation Rentals in South Portland

  • New Light-Filled 3BR w/ Gourmet Kitchen & Patio
     3br Home/Apartment
    RedAwning
    From
    $643
  • Turner Apartments
    ExcellentCountry House
    Booking.com
    From
    $152
  • WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $1,048
  • Cottage w/ Porch, Pond View
     Cabin
    RedAwning
    From
    $309
  • Old Port Style & Luxury
     Home/Apartment
    Booking.com
    From
    $321
  • WILLARD BEACH: Stunning newly RENOVATED HOUSE! 4 Mins to DT Portland.
     4br Home/Apartment
    HolidayLettings
    From
    $1,048
  • Valhalla Cottage on Peaks Island!
     Country House
    Booking.com
    From
    $324
  • Portland, Maine - East End Rental
    Good3br Home/Apartment
    HolidayLettings
    From
    $612

Check prices for these upcoming dates

South Portland Vacation Rentals with a Pool

  • Private apt 3 minute drive to Higgins Beach
    Excellent2br Home/Apartment
    Airbnb
    From
    $206
  • Loft Apartment on Tree-Lined Street in Falmouth
    ExcellentHome/Apartment
    Airbnb
    From
    $170
  • Cabin 3: "First Mates' Cabin"
    GoodHome/Apartment
    Airbnb
    From
    $146

South Portland Vacation Rentals with Wi-Fi

  • Knightville Landing - Chic Ocean Street Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $119
  • Top of the Hill So Po in law
    ExcellentHome/Apartment
    Airbnb
    From
    $98
  • Oasis on the Sea
     Home/Apartment
    Airbnb
    From
    $500
  • A Sunny 19th-Century Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $218

South Portland Pet-Friendly Vacation Rentals

  • Beautiful Seaside Island Home
     3br Home/Apartment
    HolidayLettings
    From
    $468
  • Portland Area Cottage w/OCEAN VIEWS ~ pet friendly
     3br Home/Apartment
    HolidayLettings
    From
    $885
  • Cozy Apartment at Pride's Corner on 1rst floor!
     Home/Apartment
    HolidayLettings
    From
    $192
  • Sleek condo w/ private patio - less than 2 blocks to beach/park, small dogs OK!
     2br Home/Apartment
    HolidayLettings
    From
    $283

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
92 º41
6
84 º25
5
61 º4
10
55 º7
4
50 º-17
3
68 º2
4
58 º8
3
67 º23
6
90 º33
1
91 º46
3
93 º51
4
93 º53
4
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

Vacation Rentals in South Portland

At AllTheRooms.com we have vacation rentals from all of the leading providers - Airbnb, Priceline, RedAwning and others. We have 365 vacation rentals, hotels and other accommodation types in South Portland ranging from budget options to extravagant places to stay. For those trying to save money, the cheapest place to stay in South Portland comes in at $20 per night. The average price of an accommodation is generally $207 per night.

Those needing to get some work done during their trip to South Portland can pick from 214 places to stay that provide WiFi. 35 places to stay include a breakfast. Choose from 12 accommodations that provide gym facilities, so you don't miss a single workout. If you're planning on getting to South Portland by car, be sure to choose from 209 accommodations that provide parking. We have 8 places to stay that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 79 accommodations that are designated as pet-friendly.

We combine a wide variety of South Portland accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 167 places to stay from Airbnb, 7 accommodations from Priceline and 3 places to stay from RedAwning.

227 of the accommodations in South Portland have been reviewed and rated. 79% are rated excellent or good. 93 accommodations allow instant booking.

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