South Portland holiday lettings

We found 431 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 35 homes, 11 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, 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:

  • Casco Bay Lines Ferry Terminal (1.2 mi / 2 km)
  • Aquaboggan Water Park (10.4 mi / 16.8 km)
  • Pirate's Cove (11.3 mi / 18.1 km)
  • Funtown Splashtown USA (12.3 mi / 19.8 km)
  • Seacoast Adventure (18 mi / 28.9 km)
  • Sable Oaks Golf Course (5.1 mi / 8.2 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)
  • Higgins Beach (5.8 mi / 9.3 km)
  • Pine Point Beach (8.2 mi / 13.2 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 rental?

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 rental 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. Vrbo 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 rental 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 Vrbo and the number of guests to view your holiday rental 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 rentals in South Portland?

With 41 holiday rentals that welcome pets, your furry friend can join in on your South Portland break. Use our filter tool to search our pet-friendly holiday rentals and find a stay that'll set tails wagging on Vrbo.

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 Vrbo, then spend lazy days splish-splashing around in a swimming pool that's exclusively for you.

What are popular rental amenities in South Portland?

When it comes to rental amenities that guests are on the lookout for in South Portland, a swimming pool, a nearby waterfront and tennis rank highest. With Vrbo holiday rentals, 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 rentals 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 rentals 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 rentals in South Portland?

You can pick from 15 one-bedroom rentals in South Portland. Whether you're searching for a comfy cottage or a cabin, Vrbo'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 rentals 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.

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