Discover a selection of 306 vacation rentals in South Portland, ME that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $140 per night, and houses and cottages are popular options for a stay in South Portland. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — South Portland
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Destination guide

The friendly area of South Portland awaits your stay

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

Things to do

Sightseeing in and around South Portland

Are you hoping to find top things to see and do in the city? Venture out of your vacation home and check out everything that makes South Portland a fun place to get away. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Casco Bay Lines Ferry Terminal (1.2 mi / 2 km)
  • Sable Oaks Golf Course (5.1 mi / 8.2 km)
  • Aquaboggan Water Park (10.4 mi / 16.8 km)
  • Dunegrass Golf Club (11.2 mi / 18 km)
  • Funtown Splashtown USA (12.3 mi / 19.8 km)
  • Nonesuch River Golf Club (6.3 mi / 10.1 km)
Natural features

Exploring the natural landscape of South Portland

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in South Portland. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Willard Beach (0.7 mi / 1.1 km)
  • East End Beach (1.9 mi / 3 km)
  • Eastern Promenade (1.9 mi / 3.1 km)
  • Higgins Beach (5.8 mi / 9.3 km)
  • Pine Point Beach (8.2 mi / 13.2 km)
  • Prouts Neck (8.3 mi / 13.4 km)
How to get there

Transportation to and around South Portland

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 3.5 mi (5.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Sanford, ME (SFM-Sanford Seacoast Regional), which is 28.8 mi (46.3 km) away.

What are the top vacation rentals in or near South Portland?

The heart wants what the heart wants, and right now that's a vacation. It's time to pack your suitcase and retreat to one of these top vacation rentals in or near South Portland:

  • "Henry” Penthouse Suite: Amazing Views" is a hit with guests. Around 2 miles from South Portland, it has 2 bedrooms and plenty of handy amenities, including a washing machine and a nearby marina.
  • Alternatively, get comfortable at "Chic One Bedroom Apartment In Portland's Arts District". Around 2 miles from the heart of South Portland, it has 1 bedroom and features internet services and winery tours.

For even more great options, use the search bar at the top of the page to find the perfect South Portland vacation rental for you.

Can I find log cabins to rent in or near South Portland?

Select a beautiful log cabin from the many scattered in or around South Portland and you'll soon be inside your wooden sanctuary, tasty tipple in hand, sitting in front of a roaring fire. But adventure will be right there on your doorstep too. These cabins offer the perfect blend of comfort and fun:

  • "Cozy Log Cabin - Walking Distance To Morse Mountain And 3 Miles From Popham Beach": Enjoy a week resting and relaxing at this great escape in the middle of nature. Once you've recharged, enjoy surfing and boogie boarding or tennis, which are among the best activities in this area.
  • "Year Round Log Cabin Built In 1989 On Long Lake - 2": Stay in and enjoy the relaxed vibe or have a go at some of the fun activities nearby, including water skiing and kayaking. Chill or active, the choice is yours.

What are the top-rated vacation rentals for weekend getaways in or near South Portland?

If you've been busier than a bee in a garden lately, you deserve to escape for a few glorious days. Leave work early on Friday and head for one of these weekend getaways in or near South Portland:

  • Get comfy at "Maine Oceanfront Home". Located roughly 19 miles to the northeast of South Portland, this cozy escape has all you need for a chilled out stay, including a phone and a fridge.
  • Or, cram a few clothes into your overnight bag and head off to "Percival” Penthouse Suite: Breathtaking Views". This great getaway is around 2 miles northeast of South Portland and has a free nearby fitness center and heating.

Can I find studio apartments for rent in and around South Portland?

Studio apartments are a simple yet stylish choice, ideally suited for traveling couples or solo adventurers. Spend your days getting acquainted with your surroundings and your nights chilling out in your comfy hideaway. These properties in or near South Portland are guaranteed to please:

  • Get away on your own or take a friend along to "Chic One Bedroom Apartment In Portland's Arts District". You'll have plenty of amenities to make your stay comfortable, including a hair dryer and a living room.
  • "Historic Condo With Casco Bay Views" is another superb stay, offering all you could want for the ideal South Portland escape. Handy amenities here include a microwave oven and a nearby laundromat.

Can I find short term rentals in or near South Portland?

From cozy apartments to sprawling vacation homes, Vrbo has your quick break sorted. Here are two of our popular picks in and around South Portland:

  • If you only need to stay a few nights, "Percival” Penthouse Suite: Breathtaking Views" is a great choice. It's not far from the center of South Portland, so you'll be within easy reach of all the top sights.
  • Alternatively, spend a few relaxing nights at "Margaret” Penthouse Suite: Amazing Views Of Casco Bay". This conveniently located property makes exploring the local sights easy.

What are the best romantic weekend getaways in or near South Portland?

Whether spent in a cabin, a cottage or a treehouse, a romantic weekend getaway is a wonderful way to spice up your love life. Whisk your partner off for a couple of leisurely days at one of these top escapes in or near South Portland:

  • Put on some relaxing tunes and slow dance the nights away at "Henry” Penthouse Suite: Amazing Views". Around 2 miles from South Portland, this property has all you need for a romantic weekend getaway, including a nearby bay and winery tours.
  • "Chic One Bedroom Apartment In Portland's Arts District" is another terrific option that's guaranteed to impress. It's about 2 miles from South Portland and comes with winery tours and a nearby bay.

What are the best large group vacation rentals in or near South Portland?

Share your trip and boost your odds of having fun. Whether you're planning an epic escape with buddies for a family get-together, you'll have your choice of large group vacation rentals in and around South Portland:

  • A host of amenities including a firepit and an ocean view make "New Well Built Elegant Home On The Water 2 Miles To Freeport" a standout. This generous getaway has 6 bedrooms and sleeps up to 12 people. From central South Portland, it's around 16 miles away to the northeast.
  • Invite up to 18 of your favorite people to "Stunning 2nd And 3rd Floor Apts - Usm Area" and fill its spaces with love and laughter. This top option has 8 bedrooms and is around 2 miles to the north of central South Portland. It's packed with features to keep your large group comfortable and content, including a kitchen and an oven.

What are the best houses for rent with a pool in or near South Portland?

Of all the conveniences a vacation rental can offer, a pool promises the most fun. Check out these houses for rent with a pool in or near South Portland and spend your time splashing about. Just don't forget your inflatable unicorn:

  • Pack your swimsuit and book a few days at "Maine Getaway: Bright Beautiful Back Cove House Near Woodfords Corner And Old Port". There are plenty of other great amenities here, including a nearby bay and outdoor furniture.
  • "The Globe House On Munjoy Hill" is the type of place you go to leave it all behind and make the most of your surroundings, starting with its inviting pool. Childrens activities and a fridge are also on hand to make your visit as comfortable as possible.

Wondering what the weather's like in South Portland? It has a humid continental climate, with average summertime temperatures ranging from 60 ºF to 75 ºF. If you're seeking more inspiration on places to stay in this epic destination, use the search bar at the top of the page and adjust the filters to check out our entire range of South Portland vacation rentals.

What are the best large family vacation rentals in or near South Portland?

It's always more fun when you share precious moments with the ones you love the most. Whether you're organizing a family reunion or getting away with good friends, Vrbo has a large vacation rental to suit your style. Here are two of our best in and around South Portland:

  • Sleeping as many as 11 guests in 4 bedrooms, "Maine Oceanfront Home" is the ideal place for some family time. This retreat is 19 miles to the northeast of South Portland and has amenities such as a kitchen and a fridge.
  • "New Well Built Elegant Home On The Water 2 Miles To Freeport" also has the space you need to connect with loved ones. This option is around 16 miles to the northeast of South Portland, and accommodates as many as 12 guests in its 6 bedrooms. A smart TV and on-site watersports will help keep everyone happy and comfortable.

When it's time to venture outside and explore, there are plenty of family-friendly attractions nearby to keep everyone entertained. Children's Museum of Maine, Portland Observatory and Fort Williams Park should be at the top of your itinerary.

Can I find family cabin rentals in or near South Portland?

Vacation with the kiddos in a family cabin rental in or near South Portland and make some wonderful memories together. Check out these options:

  • "Secluded Casco Bay Waterfront Cabin" - Located around 17 miles northeast of central South Portland, this family-friendly escape offers amenities like cable/satellite TV services and outdoor furniture.
  • "Cabin - Quintessential Frye Island On Beautiful Sebago Lake" - Another awesome choice, this property comes with a stereo, towels and more. You'll find it around 19 miles to the northwest of South Portland.

For more options, use the search bar at the top of the page and adjust the filters to find the South Portland vacation rental that's perfect for your needs.