South Portland holiday lettings

We found 450 holiday rentals — enter your dates for availability

Discover a selection of 27 homes, 16 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.

Holiday rentals with weekly discounts - South Portland

Showing deals for:29 May - 5 Jun

Image gallery for Large, light filled 4 bedroom house - walk to ocean and ferry

Heron's Perch on Peaks' Island
9.8 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island

9% off
Price is £3,723
for 7 nights, 1 home
£532 per night
includes taxes & fees
Large, light filled 4 bedroom house - walk to ocean and ferry

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Why visit South Portland

  • Beautiful beaches: South Portland boasts stunning beaches, perfect for a relaxing day by the sea.
  • Historic lighthouses: Explore the iconic lighthouses that showcase the area's rich maritime heritage.
  • Charming downtown: Enjoy a vibrant downtown area filled with shops, cafes, and local attractions.
  • Scenic views: Take in breathtaking views at the Eastern Promenade, ideal for leisurely walks.
  • Variety of accommodations: Choose from delightful holiday rentals, including cottages and modern condos.

Popular types of accommodation in South Portland

Vrbo offers a variety of holiday rentals in South Portland, perfect for British travellers seeking comfort and convenience. Popular options include houses, charming cottages, and modern condos. Whether you’re searching for apartment rentals or a cozy retreat, you’ll find available apartments that cater to your needs in Portland, Maine. Explore our collection to discover the ideal accommodation for your next getaway.

  • Houses: The top choice for visitors to South Portland, offering spacious and comfortable stays for families, friends, or couples.
  • Cottages: A charming option that provides a quaint and cosy atmosphere, ideal for a peaceful retreat.
  • Condos: A popular selection for those seeking modern amenities and the convenience of self-catering.
  • Apartments: A practical choice for solo travellers or couples, offering a homely feel in the heart of the city.
  • Cabins: Perfect for nature enthusiasts, these rustic lodgings create a serene escape amidst the great outdoors.**

Top attractions near South Portland

South Portland is an ideal destination for families, business travellers, and those seeking a city-themed holiday. Visitors can explore a variety of attractions, including beautiful beaches, entertainment arenas, and historic lighthouses, all of which provide a rich cultural experience. Whether you're after a relaxing beach day or a glimpse into the area's heritage, South Portland offers something for everyone to enjoy.

  • Portland Head Light: A stunning historic lighthouse located 1.2km from South Portland, offering breathtaking coastal views and a glimpse into maritime history. The surrounding park features scenic walking trails and picnic spots, perfect for enjoying the culture vibes.
  • Portland Museum of Art: Situated 621m away, this art museum showcases an impressive collection of American and European artworks. Its vibrant exhibitions and cultural events make it a must-visit for art enthusiasts.
  • Cross Insurance Arena: Only 621m from South Portland, this entertainment venue hosts a variety of events, from concerts to sports. It’s a fantastic place for family fun and lively entertainment.

Things to do recommended for couples

For a romantic getaway in South Portland, enjoy the lively atmosphere at Thompson's Point music concert, indulge in luxury at the Portland Club, or embark on an adventurous water sports experience with Capt Lyman Stuart, LLC. Each offers a unique vibe perfect for couples.

Things to do recommended for families

During your family vacation in South Portland, you can enjoy a thrilling game at Hadlock Field, explore the fascinating Portland Observatory, and unwind at Fort Williams Park, all conveniently located within 1.2km. These experiences promise fun, entertainment, and relaxation for the whole family!

Things to do recommended for groups

Explore the Maine Mall for shopping and entertainment, catch a show at the State Theatre for a cultural evening, or enjoy a round at Sable Oaks Golf Course for some outdoor sports fun. South Portland offers a delightful mix for group travellers seeking local experiences!

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

If you're travelling with a group, family, pets, or seeking longer stays, it's important to filter your search according to your priorities. Here are some helpful tips for booking with Vrbo.

  • Traveling to South Portland with a group: Think about how many bedrooms you will require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to South Portland with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to South Portland: For many, a family holiday isn’t truly fulfilling without their four-legged companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting South Portland: If you're in search of holiday rentals with special offers for extended stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near South Portland

South Portland, Maine, offers an inviting blend of family-friendly attractions and vibrant urban experiences. Just minutes from Portland, you can explore the charming downtown, enjoy the scenic views at Eastern Promenade, and indulge in retail therapy at the local shopping plaza. With a warm atmosphere and a rich cultural backdrop, South Portland is the perfect destination for a memorable vacation, whether you're seeking romance, business, or simply a delightful getaway.

  • Portland: Situated a mere 1.2km from South Portland, the city of Portland is renowned for its stunning outdoor scenery and family-friendly atmosphere. Visitors can indulge in a variety of activities, including exploring local theatres, enjoying events at the arena entertainment facility, and shopping at the vibrant mall centre. The area is also home to beautiful beaches, a family beach, and picturesque lakes, making it a perfect destination for nature lovers and those seeking a bit of adventure.
  • Downtown Portland: Just 621m from South Portland, Downtown Portland offers a delightful blend of family, outdoor, and romantic experiences. This neighbourhood is alive with cultural activities, featuring theatres and music concerts that cater to all tastes. The proximity to stunning beaches, including family-friendly spots and serene lakes, enhances the appeal, providing visitors with a scenic backdrop for their adventures.
  • Old Port: Also located 621m from South Portland, Old Port is a charming neighbourhood that exudes an entertainment-themed vibe, perfect for families and visitors seeking fun. The area boasts a variety of venues, including an arena entertainment facility and theatres, along with appealing shopping mall centres. With its close proximity to beautiful beaches, family beaches, and tranquil lakes, Old Port is an ideal spot to enjoy both relaxation and excitement during your stay.

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 simple

Are you aiming to save on your next holiday? It might be worthwhile to keep your travel dates flexible, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new getaways, manage your existing arrangements, or review your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • 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)
  • Aquaboggan Water Park (10.4 mi / 16.8 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 rental?
When considering a holiday rental in South Portland, Maine, the best area to stay is typically around the waterfront neighbourhood. This area offers a delightful blend of scenic views and convenient access to some of the city's top attractions. The iconic Bug Light Park is a must-visit, featuring a charming lighthouse and beautiful green spaces superb for leisurely strolls or picnics.

Another appealing neighbourhood is the Willard Square area, known for its quaint atmosphere and proximity to local shops and eateries. Here, you can enjoy the local flavour with a variety of dining options, from seafood to artisanal cafes. The nearby Scarborough Marsh is also a fantastic point of interest, superb for nature enthusiasts who wish to explore the rich wildlife and picturesque trails.

In terms of holiday rentals, there are numerous properties available across these areas, offering a range of options from cozy cottages to modern apartments.
How much does it cost to rent a holiday home in South Portland?
Prices for holiday 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 holiday 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, the area surrounding Willard Beach is highly recommended. This picturesque beach features soft sands and a charming atmosphere, making it ideal for families and groups looking for a seaside getaway. Many properties in this vicinity offer amenities such as outdoor decks with stunning views of the ocean, fully equipped kitchens for home-cooked meals, and spacious living areas great for relaxation after a day at the beach.

Another attractive option is the area near Cape Elizabeth, where you can find beautiful beach houses that provide direct access to the scenic shores of Crescent Beach State Park. These rentals often come with additional amenities, such as private outdoor spaces, fire pits for evening gatherings, and proximity to walking trails that lead to breathtaking coastal vistas.

Additionally, the nearby Spring Point Ledge Lighthouse adds a historical touch to your beach experience, with lovely walking paths around the waterfront. Rentals here frequently include features like outdoor showers, laundry facilities, and easy access to local shops and restaurants, enhancing the overall convenience for visitors.
What is the most popular type of holiday rental accomodation in South Portland?
In South Portland, holiday houses are the most popular type of holiday rental, with around 64 available throughout the area. These properties are often situated in family-friendly neighbourhoods, providing ample space for families or groups. Most holiday houses come equipped with multiple bedrooms, fully fitted kitchens, and outdoor areas for barbecues or relaxation. Additionally, there are about 40 apartments available, which cater to those seeking a more compact stay, typically featuring modern amenities, cosy living spaces, and sometimes balconies. There are also several condos and cottages, adding to the variety of accommodations.
Are there any family house rentals in South Portland?
In South Portland, there is a good selection of family-friendly house rentals, with around 17 options available. Neighbourhoods such as Knightville and Willard Beach are particularly appealing for families. Knightville features spacious homes with multiple bedrooms, allowing for comfortable group stays, and many properties come equipped with amenities like full kitchens and outdoor spaces great for barbecues or lounging.

Willard Beach is a lovely area with access to sandy shores, where families can enjoy beach activities and picnics. Visitors can also explore nearby attractions such as the scenic Bug Light Park, which offers walking trails and stunning views of the Portland skyline.

With a variety of amenities, including Wi-Fi and laundry facilities, these homes provide a convenient base for families looking to explore the beautiful coastline and local attractions.
Can I find long-stay holiday rentals in South Portland?
A long-stay holiday rental in South Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in South Portland?
In South Portland, there are several pet-friendly house rentals available to accommodate travellers with pets. Many of these properties offer convenient amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air. The rentals are often located in charming neighbourhoods, close to parks and recreational areas.

One popular area is the Willard Beach neighbourhood, which not only provides access to the beautiful beach but also features nearby parks that welcome pets. This lively community is great for those looking to enjoy coastal walks and the vibrant local atmosphere. Additionally, the area around Thomas Knight Park offers great outdoor spaces for pets to roam and play.
Are there any remote work holiday rentals in South Portland?
In South Portland, there are numerous holiday rentals suitable for remote work, with around 100 options available. This charming coastal city offers a variety of properties that cater to the needs of those looking to balance work and leisure. Many of these rentals come equipped with essential amenities such as free Wi-Fi in both rooms and public areas, ensuring a reliable connection for work-related tasks.

Travellers can expect comfortable living spaces, often featuring dedicated work areas, making it easy to set up a home office. Additionally, some properties may offer access to communal facilities such as co-working spaces or outdoor areas for relaxation during breaks.

South Portland is also conveniently located near the picturesque waterfront, where you can enjoy local parks, beautiful views of the Casco Bay, and a vibrant dining scene. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any South Portland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South Portland with parking available—perfect for families or travellers 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 holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also offer onsite parking, making it convenient for those travelling by car. For coffee lovers, rentals often feature coffee and tea makers, ensuring a warm beverage is always within reach. Additionally, some accommodations are pet-friendly, welcoming travellers with furry companions. Many rentals also provide a blender, ideal for making smoothies or other quick meals.
When is the best time to visit South Portland for a holiday rental?
The best time to visit South Portland for a holiday rental is during the peak season from June to August, with July being particularly popular. This vibrant summer period attracts a variety of travellers eager to soak up the coastal charm, enjoy the stunning beaches, and indulge in fresh seafood at local eateries.

With temperatures typically ranging from 15 to 30 degrees Celsius, visitors can comfortably engage in outdoor activities such as kayaking, hiking, and exploring the scenic waterfront. The warm weather also sets the superb stage for leisurely strolls along the picturesque promenade, where you can take in views of the Atlantic Ocean and bustling marina.

If you're looking for a more budget-friendly option, consider visiting in November. While this month may be quieter, it offers unique opportunities to experience the local culture without the crowds. Autumn in South Portland showcases beautiful fall colours, and you can enjoy a peaceful escape while still savouring the region's culinary delights.

Ultimately, your ideal time to visit South Portland will depend on whether you prefer the lively summer atmosphere filled with activities or a more tranquil experience in the autumn months.
How early should I book a South Portland holiday rental?
Book your South Portland holiday 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 holiday 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, Maine, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque waterfront area known as the Bug Light Park offers stunning views of the Portland skyline and is home to the historic Portland Breakwater Lighthouse, also known as Bug Light. This park features walking paths and picnic areas, making it a lovely spot for relaxation.

Another significant attraction is the South Portland Historical Society and Museum, where guests can learn about the region's rich history and heritage. The nearby Willard Beach is superb for those looking to unwind by the ocean, with sandy shores and scenic views of the Casco Bay Islands.

For outdoor enthusiasts, the Greenbelt Walkway provides miles of trails for walking, running, or cycling, connecting various parks and recreational areas throughout the city. Additionally, the nearby Cape Elizabeth area, with its famous Fort Williams Park and the iconic Portland Head Light, is just a short drive away and offers breathtaking coastal scenery.

In terms of dining and shopping, the Knightville neighbourhood features a range of local eateries and shops that reflect the vibrant community spirit of South Portland.
Can I change or cancel my South Portland home rental booking on Vrbo?
To find South Portland holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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