South Portland Vacation Rentals

Our Favorite Vacation Rentals in South Portland

  • Newer South Portland Cottage, 10-Min to Downtown, 30-Day Rentals
     Cottage
    RedAwning
    From
    $479
  • Old Port Class & Style
     Home/Apartment
    Booking.com
    From
    $164
  • WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $1,048
  • New Light-Filled 3BR w/ Gourmet Kitchen & Patio
     3br Home/Apartment
    RedAwning
    From
    $717
  • Haven on the Hill
     Home/Apartment
    Booking.com
    From
    $192
  • Luxurious, Fully Renovated house with Private Beach rights.
     5br Home/Apartment
    HolidayLettings
    From
    $1,201
  • Arbor Lane Delight
     Country House
    Booking.com
    From
    $264
  • Charming Downtown 1BR w/ Parking, Short Walk to Old Port
     Home/Apartment
    HolidayLettings
    From
    $356

Check prices for these upcoming dates

South Portland Vacation Rentals with a Pool

  • Swim spa under the starry night with hot tub/sauna
    Excellent3br Home/Apartment
    Airbnb
    From
    $523
  • Loft Apartment on Tree-Lined Street in Falmouth
    ExcellentHome/Apartment
    Airbnb
    From
    $105
  • Andy's Retreat-Heated pool, Hot Spring jacuzzi, AC
    Excellent4br Home/Apartment
    Airbnb
    From
    $451

South Portland Vacation Rentals with Wi-Fi

  • Portland's Best Old Port & Beaches
    Excellent3br Home/Apartment
    Airbnb
    From
    $325
  • Apartment just tastefully remodeled for your enjoyment and comfort.
    ExcellentHome/Apartment
    Airbnb
    From
    $170
  • Newly Renovated Condo in Cape Elizabeth, ME
    Excellent2br Home/Apartment
    Airbnb
    From
    $132
  • West End One Bed/Bath Urban Retreat w/ Parking
    ExcellentHome/Apartment
    Airbnb
    From
    $94

South Portland Pet-Friendly Vacation Rentals

  • Portland Area Cottage w/OCEAN VIEWS ~ pet friendly
     3br Home/Apartment
    HolidayLettings
    From
    $1,110
  • Walk to Old Port ♦ West End Condo ♦ Parking
    Excellent3br Home/Apartment
    Airbnb
    From
    $258
  • Updated Apartment in South Portland
    Excellent2br Home/Apartment
    Airbnb
    From
    $232
  • The BumbleBee Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $110

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
50°
6
62° -2°
4
55°
3
73° 24°
5
84° 37°
4
84° 47°
6
94° 57°
3
85° 47°
4
89° 38°
0
71° 32°
6
63° 13°
3
58°
8
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in South Portland. The hottest month in South Portland is June, when temperatures peak at 94 ˚F. The coolest month is November, when temperatures drop to -2 ˚F. The wettest month in South Portland is January with 8.27 inches of rain, while the driest month is April with 0.42 inches of rain.

What Expert Travelers Think

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — 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
  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa

Vacation Rentals in South Portland

Find the perfect rental for your vacation at AllTheRooms.com. We compare Airbnb, Priceline, RedAwning and others. AllTheRooms has 260 vacation rentals, hotels and other great places to stay during your time in South Portland, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. A vacation in South Portland can be budget-friendly - our cheapest price rental is available at $20 per night. A typical rental in South Portland costs on average $209 per night.

If you have to have an internet connection during your stay in South Portland, then you can choose from over 153 places to stay that have WiFi internet. 24 places to stay include a morning meal. Fitness fanatics can get a workout in during their stay by choosing from 11 accommodations that have gym facilities. If you are driving to South Portland, you'll want to pick from 152 places to stay that provide parking. We have 5 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 48 pet-friendly places to stay in South Portland, so if you're traveling with your pet you won't have any trouble.

185 of our accommodations in South Portland have been reviewed and rated. 85% are rated excellent or good. You can instantly book any of 78 places to stay right now.

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