South Portland holiday lettings

We found 473 holiday rentals — enter your dates for availability

Discover a selection of 30 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.

Holiday rentals with weekly discounts - South Portland

Showing deals for:6 Mar - 13 Mar

Image gallery for Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Relax in the private hot tub
10 out of 10, Exceptional, (66 reviews)
Exceptional
(66 reviews)

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Portland, ME

8% off
Price is £5,394
for 7 nights, 1 home
£771 per night
includes taxes & fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Find spaces that suit your style

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)
  • Aquaboggan Water Park (10.4 mi / 16.8 km)
  • Land's End Gift Shop (13.1 mi / 21 km)
  • Old Orchard Beach Parasail (14.2 mi / 22.8 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)
  • 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)
  • Scarborough Beach State Park (7.6 mi / 12.2 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?
When considering a holiday rental in South Portland, Maine, a popular area to stay in is the picturesque neighbourhood of Willard Beach. This charming area boasts stunning ocean views and a relaxed coastal vibe, making it ideal for those who wish to enjoy the beauty of Maine's coastline. Willard Beach itself is a popular spot for sunbathing, swimming, and beachcombing, while the nearby Mill Creek Park offers lovely walking paths and picnic areas, superb for a leisurely afternoon.

Another fantastic option is the Knightville neighbourhood, which is known for its vibrant arts scene and community spirit. Here, you'll find a range of local shops, cafes, and restaurants, making it a delightful place to explore. The nearby Greenbelt Walkway provides scenic views and is a great spot for walking or cycling. This area is particularly appealing for those who enjoy local culture and a sense of community.
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, Maine, one of the best areas to consider is the coastline around Willard Beach. This vibrant neighbourhood offers charming beach houses with stunning views of Casco Bay and easy access to the sandy shores. Many properties here come equipped with amenities such as outdoor decks, barbecue facilities, and spacious living areas, making them great for families or groups looking to relax by the sea.

Additionally, the nearby Ferry Beach area is also a great option, where you'll find quaint cottages and larger homes that often feature amenities like private patios, picnic areas, and fully stocked kitchens. This area is great for those who enjoy beach activities and want to be close to local attractions, including the scenic Greenbelt Walkway, which offers beautiful views and walking paths along the coast.
What is the most popular type of holiday rental accomodation in South Portland?
In South Portland, holiday houses are the most popular type of rental, with approximately 45 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups. Additionally, there are around 13 apartments scattered across the city, often found in convenient locations close to local attractions and waterfront views. For those seeking a cozier option, several cottages and condos are also on offer, providing a comfortable and home-like atmosphere.
Are there any family house rentals in South Portland?
In South Portland, there are numerous family-friendly rentals available, with around 35 properties to choose from. This vibrant area offers a variety of spacious homes suitable for larger groups or families, often featuring amenities such as well-equipped kitchens, comfortable living rooms, and outdoor spaces for children to enjoy.

Many of these residences are conveniently located near popular attractions, such as the picturesque Willard Beach, superb for seaside outings, and the scenic Greenbelt Walkway, which provides opportunities for family strolls and bike rides. Additionally, visitors can explore nearby parks and playgrounds, making it an ideal locale for families seeking both relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in South Portland?
In South Portland, there are several holiday homes available for rent that feature pools and hot tubs. This charming coastal city offers a variety of neighbourhoods where these properties can be found, including the picturesque Cape Elizabeth area, known for its stunning coastal views and proximity to beautiful beaches.
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, providing ample options for travellers looking to stay in this charming coastal city. Many of these properties come equipped with modern amenities, such as fully stocked kitchens, spacious living areas, and outdoor spaces ideal for enjoying the lovely Maine weather.

The Willard Beach area is particularly appealing for pet owners, as it features scenic walking paths and sandy shores where dogs can enjoy the outdoors. Additionally, the area is home to several pet-friendly cafes and local shops, ideal for visitors with pets.
Are there any remote work holiday rentals in South Portland?
In South Portland, there are numerous remote work holiday rentals available, with around 46 options to choose from. This vibrant coastal city offers a range of properties that cater to the needs of remote workers. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces including desks and comfortable chairs, and in some cases, additional features like computer monitors and safes for secure storage.

Travellers can expect a variety of accommodations, from modern apartments near the waterfront to charming houses in residential neighbourhoods. The city boasts convenient access to local cafes and co-working spaces, providing additional options for those who may prefer a change of scenery while working. 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 rental amenities include complimentary Wi-Fi in the rooms, fully equipped kitchens, and convenient access to third-party internet services. Many properties feature essential appliances such as microwaves and ovens, allowing guests to prepare their own meals.
When is the best time to visit South Portland for a holiday rental?
The best time to book a holiday rental in South Portland is during the summer months, particularly in July. This period marks the peak season, when visitors flock to the area to enjoy its beautiful coastline, vibrant local culture, and a variety of outdoor activities. The warm temperatures, typically ranging from the mid-teens to low 20s Celsius, create ideal conditions for exploring nearby beaches, parks, and scenic trails.

During July, South Portland buzzes with energy, offering numerous events and festivals that showcase the local community and its rich maritime heritage. It's a fantastic time for those who relish lively atmospheres, as the city welcomes both tourists and locals alike to enjoy outdoor dining and waterfront activities.

For travellers seeking a more budget-friendly experience, November presents a unique opportunity to enjoy South Portland's charm without the crowds. Although the weather cools down, with temperatures averaging around 5-10 degrees Celsius, visitors can appreciate the beauty of the coastline in a quieter setting, making it a superb time for peaceful walks along the shore or cozying up in a local café.
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, visitors can enjoy a range of attractions that highlight the area's coastal charm. The picturesque Willard Beach, known for its sandy shores and stunning views of Casco Bay, is a popular spot for both relaxation and water activities. Holiday rentals in the nearby Willard Square neighbourhood provide convenient access to the beach, as well as local eateries and cafes.

The Greenbelt Walkway offers a scenic trail that runs through various neighbourhoods, great for walking or cycling while enjoying the natural beauty of the area. In the waterfront district, visitors can explore the charming shops and restaurants along the South Portland Promenade, with the chance to witness the bustling activity of the working waterfront.
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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