South Portland vacation rentals

We found 450 vacation rentals — enter your dates for availability

Discover a selection of 31 homes, 13 apartments, and other vacation rentals in South Portland that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, including air conditioning and WiFi. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - South Portland

Showing deals for:Mar 27 - Apr 3

Image gallery for Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Pool
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough

8% off
Price is $429
$3,005 for 7 nights
All fees included
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

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Find out more about South Portland

Why visit South Portland

  • Beautiful Beaches: Enjoy stunning coastal views and relaxing days on South Portland's picturesque beaches.
  • Historic Attractions: Explore charming historic houses that showcase the city’s rich heritage.
  • Vibrant Downtown: Experience the lively atmosphere with shops, restaurants, and entertainment options.
  • Family-Friendly Activities: Engage in various activities suitable for all ages, ensuring fun for the whole family.
  • Cozy Accommodations: Choose from a range of vacation rentals, including cottages and modern condos, for a comfortable stay.

Popular types of accommodation in South Portland

Planning your getaway to South Portland? You're in for a treat. This charming coastal city offers a variety of vacation rentals to suit your needs, including houses, cozy cottages, and modern condos. Whether you're looking for house rentals or apartments in South Portland, you'll find plenty of options that provide comfort and convenience. Explore our selection of vacation rentals in South Portland and start your adventure today.

  • Houses: The top choice for visitors to South Portland, offering spacious and comfortable settings for families or groups.
  • Cottages: A close second, these charming and cozy retreats provide a delightful atmosphere for a relaxing getaway.
  • Condos: Third in popularity, condos offer modern amenities and often stunning views, ideal for a stylish stay.
  • Apartments: Fourth on the list, apartments provide a convenient and homely option for travelers seeking flexibility.
  • Cabins: Rounding out the list, cabins offer a rustic experience, perfect for those looking to connect with nature.**

Top attractions near South Portland

South Portland, Maine, is an ideal destination for family vacations, business trips, and city explorations. Visitors can enjoy a variety of attractions, including beautiful beaches, historic houses, and entertainment arenas. With a focus on culture and family experiences, South Portland offers something for everyone, ensuring a memorable getaway for travelers of all kinds.

  • Portland Head Light: A historic lighthouse that stands majestically on the coast, offering stunning views of the Atlantic Ocean. Its picturesque backdrop makes it a perfect spot for photography and reflection, rich in maritime history.
  • Cross Insurance Arena: A vibrant entertainment venue hosting a variety of events, from concerts to sporting events. Ideal for family outings, it features a lively atmosphere that brings the community together.
  • Portland Museum of Art: This art museum showcases an impressive collection of American and European art, providing a cultural oasis that enriches visitors' appreciation of art and history.

Things to do recommended for couples

For a romantic getaway in South Portland, enjoy a concert at Thompson's Point for lively entertainment, indulge in luxury at the Portland Club, or embark on an adventurous parasailing experience at Old Orchard Beach. Each spot offers a unique atmosphere perfect for couples seeking memorable moments together.

Things to do recommended for families

In South Portland, families can cheer on local teams at Hadlock Field, unwind at the scenic Fort Williams Park, and dive into fun at Aquaboggan Water Park. Each destination offers a unique blend of sports, relaxation, and adventure for everyone to enjoy.

Things to do recommended for groups

Explore the Maine Mall for shopping and entertainment, enjoy a cultural night at the State Theatre, just a mile away, or take a scenic drive to the LL Bean Flagship Store, 16 miles from South Portland, for unique outdoor gear and experiences.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in South Portland

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to keep in mind.

  • Traveling to South Portland with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to South Portland with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to South Portland: For many, a family vacation wouldn't be the same without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting South Portland: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near South Portland

South Portland, Maine, offers a delightful blend of family-friendly activities and urban charm. Visitors can enjoy stunning waterfront views, explore the vibrant downtown area, and experience the serene atmosphere of nearby neighborhoods. A short trip to downtown Kennebunkport promises romantic scenery and cultural experiences. Whether you're here for business or leisure, South Portland is the perfect base for your Maine adventure, providing a warm, welcoming vibe and plenty of opportunities for exploration.

  • Portland: Located a mere 2 miles from South Portland, Portland is a vibrant city known for its stunning outdoor landscapes and family-friendly activities. Visitors can enjoy a variety of attractions, from picturesque beaches to serene lakes. The city boasts a thriving arts scene, with theaters and arena entertainment facilities offering a range of performances. Shopping enthusiasts will appreciate the local mall centers, while nature lovers can explore the scenic waterfront parks that make Portland a must-visit destination.
  • Downtown Portland: Just 1 mile away from South Portland, Downtown Portland is a bustling neighborhood that perfectly blends family fun with outdoor adventures and romantic experiences. Visitors can catch a live music concert or enjoy a night out at one of the many theaters and arena venues. The area is also home to beautiful beaches and family-friendly lakes, providing ample opportunities for relaxation and recreation. Strolling through the downtown streets, you’ll find an array of restaurants and cafes that cater to all tastes.
  • Old Port: A charming neighborhood located 1 mile from South Portland, Old Port is a lively area known for its entertainment-themed experiences. With a mix of theaters, arena facilities, and shopping options, there's something for everyone. Families will enjoy the proximity to beautiful beaches and lakes, perfect for a day of fun in the sun. The waterfront area is particularly delightful, featuring cobblestone streets lined with unique shops and eateries, making it an ideal spot for exploring and enjoying the local culture.

Best time to go to South Portland

If you're planning a trip to South Portland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.6°F (-3.0°C)Light RainMostly SunnySlightly LowSlightly Low
February27.5°F (-2.5°C)Light RainMostly SunnyAverageSlightly Low
March33.8°F (1.0°C)Light RainMostly SunnyAverageSlightly Low
April43.7°F (6.5°C)Light RainMostly SunnyAverageAverage
May53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
June61.3°F (16.3°C)Light RainMostly SunnySlightly HighSlightly High
July68.2°F (20.1°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
September61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
October52.3°F (11.3°C)Light RainMostly SunnyAverageAverage
November41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage
December33.4°F (0.8°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, if you book a longer stay, you often can enjoy substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels, pick up right where you left off, or easily manage your itineraries. You can find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 for a relaxing getaway.

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:

  • 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)
  • Seacoast Adventure (18 mi / 28.9 km)
  • Aquaboggan Water Park (10.4 mi / 16.8 km)
  • Old Orchard Beach Parasail (14.2 mi / 22.8 km)

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)
  • 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)

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 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 vacation rental?
When planning a vacation rental in South Portland, Maine, one of the best areas to consider is the Willard Beach neighborhood. This charming coastal community is known for its picturesque beach, making it a great spot for those who enjoy sunbathing, swimming, and beachcombing. You'll find a variety of vacation rental options here, ranging from cozy cottages to modern homes with ocean views, ensuring there's something to suit every taste and budget.

Another great option is the Knightville neighborhood, which boasts a vibrant, artsy atmosphere. This area is known for its energetic mix of restaurants, cafes, and shops, making it a delightful place to explore. It's also conveniently located close to attractions like the Maine Mall and the scenic Greenbelt Walkway, which offers beautiful views and walking paths along the waterfront.
How much does it cost to rent a vacation home in South Portland?
Prices for vacation rentals in South Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in South Portland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for South Portland vacation house rentals?
You can find great discounts on house rentals in South Portland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in South Portland?
For renting a beach house in South Portland, Maine, the area around Willard Beach is a fantastic choice. This neighborhood offers a charming seaside atmosphere with beautiful sandy shores and picturesque views of the ocean. Many beach houses here come with amenities such as spacious decks for outdoor dining, grills for barbecuing, and fully equipped kitchens, making them great for families or groups looking to enjoy a beach getaway.

Additionally, the nearby Spring Point Ledge Lighthouse adds a scenic element to the area, creating a wonderful backdrop for leisurely strolls along the coastline. Properties close to this landmark often feature private access to the beach and easy access to walking paths. The Willard Square area also hosts local shops and eateries, providing convenience for travelers to explore local cuisine and culture.

In the surrounding neighborhoods, such as Cape Elizabeth, you can find rentals that offer a blend of spacious interiors and outdoor living spaces, including fire pits and gardens. These homes are often situated near nature reserves and coastal trails, great for those who enjoy outdoor activities like hiking and birdwatching. Find your rental near the beach in South Portland.
What is the most popular type of vacation rental accomodation in South Portland?
In South Portland, vacation houses are the most popular type of rental, with about 34 available throughout the city. These houses typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also include outdoor spaces such as decks or patios, superb for enjoying the coastal breeze. Additionally, there are around 13 apartments in the area, which offer a more compact and convenient option for couples or solo travelers, often equipped with modern amenities and easy access to local attractions.
Are there any family house rentals in South Portland?
In South Portland, Maine, families will find a variety of vacation rentals available, with around 26 properties suited for groups. Neighborhoods like Cape Elizabeth and Knightville offer spacious homes that cater to family needs. Many of these residences boast full kitchens, allowing for easy meal preparations, and cozy living areas that create a welcoming environment for relaxation after a day of exploring.

Properties in Cape Elizabeth are often close to scenic spots like Crescent Beach State Park, where families can enjoy sandy shores and nature trails. Meanwhile, Knightville features a vibrant community atmosphere, with local shops and eateries within walking distance, superb for those looking to immerse themselves in the local culture.
Can I rent a vacation home with a pool or hot tub in South Portland?
In South Portland, there are several vacation homes available for rent that come with pools and hot tubs, providing a relaxing escape for travelers. The city features charming neighborhoods such as Willard Beach, known for its scenic coastal views, and the bustling Knightville area, which offers easy access to local shops and dining.

Travelers can expect amenities such as private pools, outdoor hot tubs, spacious patios, and fully equipped kitchens, ideal for both relaxation and entertaining. Some properties may also include fire pits and outdoor dining areas, great for enjoying the pleasant Maine evenings.
Can I find long-stay vacation rentals in South Portland?
A long-stay vacation rental in South Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in South Portland?
In South Portland, travelers will find a variety of pet-friendly house rentals available, with around 30 options to choose from. Many of these homes come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces like decks or gardens, making them ideal for families or groups traveling with pets.

The Willard Beach area is particularly attractive, offering easy access to sandy shores and scenic walking paths along the coastline. Nearby, the Greenbelt Walkway provides a lovely space for pet owners to enjoy leisurely strolls with their furry friends. Additionally, the charming neighborhoods of Knightville and Ferry Village have local shops and cafes that welcome pets, ideal for visitors looking to explore the area. See all pet-friendly rentals in South Portland.
Are there any remote work vacation rentals in South Portland?
In South Portland, there are numerous remote work vacation rentals available, with around 45 options to choose from. This vibrant coastal city offers a mix of modern amenities and charming local attractions, making it an excellent choice for remote workers. Most rentals in the area come equipped with essential remote work amenities such as Wi-Fi, dedicated desks, comfortable desk chairs, and even office spaces, ensuring a productive environment. Many properties also feature additional comforts like full kitchens, laundry facilities, and outdoor areas for relaxation after work hours.

Travelers can enjoy the nearby waterfront parks and trails, great for a quick escape during breaks. Additionally, the proximity to local cafes and restaurants provides convenient options for meals or a change of scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any South Portland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in South Portland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in South Portland?
In South Portland, popular vacation rental amenities include WiFi, kitchens, blenders, coffee or tea makers, and pet-friendly options. These amenities cater to the needs of travelers looking for convenience and comfort during their stay. Many rentals provide well-equipped kitchens for home-cooked meals, while WiFi ensures guests can stay connected. The inclusion of blenders is a nice touch for those who enjoy smoothies or cooking, and the option for pets allows for a more inclusive travel experience.
When is the best time to visit South Portland for a vacation rental?
The best time to visit South Portland for a vacation rental is during the peak summer months of June through August. This vibrant season attracts visitors seeking a blend of outdoor activities, coastal charm, and cultural experiences. With warm temperatures ranging from the mid-60s to mid-80s Fahrenheit, it's ideal for enjoying beach days at Willard Beach or exploring the scenic trails of nearby parks.

July stands out as the most popular month, bringing a lively atmosphere filled with summer festivals, farmers' markets, and various local events. Travelers can engage in the local culture while savoring fresh seafood and taking in the stunning views of Casco Bay.

For those looking for a more budget-friendly option, November offers a quieter experience.
How early should I book a South Portland vacation rental?
Book your South Portland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in South Portland?
In South Portland, visitors can enjoy a variety of attractions that highlight the area's coastal charm and vibrant community. The scenic Willard Beach is a popular spot for sunbathing and swimming, and the nearby Willard Square offers quaint cafes and shops superb for a leisurely afternoon.

The Greenbelt Walkway provides a beautiful trail for walking and biking, connecting various parks and neighborhoods, including the picturesque Bug Light Park, where travelers can admire the historic lighthouse and stunning views of the Portland skyline.

For a taste of local culture, the South Portland Historic Society Museum showcases the city's rich history and heritage.
Can I change or cancel my South Portland home rental booking on Vrbo?
To find South Portland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the South Portland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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