South Portland holiday rentals

We found 477 holiday rentals — enter your dates for availability

Discover a selection of 55 homes, 14 apartments and other holiday rentals in South Portland that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The friendly area of South Portland awaits your stay

The ocean views and surrounding scenery provide a peaceful ambience to your holiday home in South Portland. This welcoming city is known for its shopping, restaurants and sporting events. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around South Portland

Are you looking for attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that makes South Portland a fun spot to go on holiday. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Aquaboggan Water Park (10.4 mi / 16.8 km)
  • Dunegrass Golf Club (11.2 mi / 18 km)
  • Pirate's Cove (11.3 mi / 18.1 km)
  • Funtown Splashtown USA (12.3 mi / 19.8 km)
  • Old Orchard Beach Parasail (14.2 mi / 22.8 km)
  • Happy Wheels Skate Center (5.4 mi / 8.8 km)

Exploring the natural landscape of South Portland

Whether you're an adventurous traveller or just want to appreciate the scenery, South Portland is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Willard Beach (0.7 mi / 1.1 km)
  • East End Beach (1.9 mi / 3 km)
  • Eastern Promenade (1.9 mi / 3.1 km)
  • Sand Beach (2.1 mi / 3.4 km)
  • Thompson's Point (2.6 mi / 4.2 km)
  • Higgins Beach (5.8 mi / 9.3 km)

Transport to and around South Portland

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 3.5 mi (5.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 28.3 mi (45.5 km) away.

Frequently asked questions

What is the best area to stay in South Portland when booking a holiday home?
Willard is one of the more in-demand neighbourhoods to book a holiday home in South Portland. Spend your getaway here to delight in the privacy and comfort that comes with having a whole place to yourself.
What is the most popular type of holiday home accommodation in South Portland?
According to our research, houses are the most popular property type in South Portland. But as you’d expect, everyone’s idea of an awesome trip is bound to be different. Stayz has holiday homes of all shapes and sizes, so you’re sure to find the perfect match.
How much does it cost to rent a holiday home in South Portland?
The average price for a holiday home in South Portland is determined by several factors, like season, property type and length of stay. Whether you’re searching for a sprawling villa with space for extended family or a quaint cottage for you and your other half, just enter your travel dates to view stays with unbeatable value.
How much does it cost to rent a beach house in South Portland?
Prices for beach houses in South Portland can vary depending on the size and type of the property and time of year you’re travelling. Simply enter your dates of travel into Stayz and the number of guests to view your holiday home options and prices. From there you can use the filters to narrow your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in South Portland?
With 41 holiday homes that welcome pets, your furry friend can join in on your South Portland break. Use our filter tool to search our pet-friendly holiday homes and find a stay that’ll set tails wagging on Stayz.
Can I rent a house with a pool in South Portland?
Add another level of fun to your adventure by staying in one of the 16 houses with a private pool in South Portland. Use our search filter to find properties with pools on Stayz, then spend lazy days splish-splashing around in a swimming pool that’s exclusively for you.
What are popular home amenities in South Portland?
When it comes to home amenities that guests are on the lookout for in South Portland, a swimming pool, a nearby waterfront and tennis rank highest. With Stayz holiday homes, you’ll enjoy options to fit your taste and style, whether you’re travelling with family, friends or even pets.
Are there large group holiday homes in South Portland?
Choose from six holiday homes in South Portland that can accommodate 10 or more people. Whether you’re planning a get-together with extended family or a special event, there’s enough room to get your loved ones together under one roof.
Are there holiday homes in South Portland that welcome kids?
South Portland has 41 family-friendly holiday homes. And securing a stay that welcomes children is a cinch with our “Properties good for families” filter. On top of having the whole place to yourselves, you’ll get conveniences and perks such as bunk beds, yards and private pools.
What are the top attractions for families in South Portland?
Keeping the kiddos entertained during your stay in South Portland is simple with these fabulous family-friendly attractions:

  • Higgins Beach
  • East End Beach
  • Pine Point Beach

Are there one-bedroom holiday homes in South Portland?
You can pick from 15 one-bedroom homes in South Portland. Whether you’re searching for a comfy cottage or a cabin, Stayz’s one-bedroom properties are perfect if you don’t need a lot of space. One of the perks of having your own pad? You won’t need to share your getaway with strangers.
Can I find two-bedroom holiday homes in South Portland?
Select from nine two-bedroom homes in South Portland. Give your little ones the second room or fill it with a couple of your besties. There’s a comfy spot for whoever’s fortunate enough to be joining your journey.
Are there holiday homes with WiFi in South Portland?
There are 11 holiday homes with WiFi in South Portland. If you’d like to disconnect from the world while on holiday, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in South Portland?
Decide on your travel dates and then make use of our filters to see holiday homes with air conditioning in South Portland on Stayz. With 36 air-conditioned properties available, you can look forward to a cool and comfy break.
How old do you have to be to rent a holiday home in South Portland?
The minimum age is typically 16, 18 or 21. It can vary from property to property on Stayz, so look at the rules of your preferred South Portland stay before making a booking.
How long can I rent a holiday home in South Portland for?
The amount of time you can rent a South Portland holiday home for is down to each property. Just tap in your dates of travel to find available options offering extended stays. They have all you need to make your extended holiday more comfortable like laundries and air conditioning. Some holiday homes might also offer discounted weekly or monthly prices, so you can stay longer for less money.

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