South Portland holiday rentals

We found 470 holiday rentals — enter your dates for availability
Discover a selection of 26 homes, 18 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:25 Dec - 1 Jan

Back yard
Willard Beach
Dining
Living area
Exceptional
(72 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
AU$4,386
for 7 nights, 1 home
AU$627 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Private kitchen
Interior
Interior
Terrace/patio
Exceptional
(17 reviews)

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

Scarborough

8% off
AU$6,338
for 7 nights, 1 home
AU$905 per night
includes taxes & fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Private kitchen
Outdoor dining
Exterior detail
The living room leads out to a private deck with a dining table that seats 4.
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
AU$3,923
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
Living area
Marina
Living area
Dining
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
AU$2,553
for 7 nights, 1 apartment
AU$365 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Private kitchen
Living area
Dining
Interior
Exceptional
(134 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

12% off
AU$2,943
for 7 nights, 1 apartment
AU$420 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Large open concept living space with tall sloped celling and a loft.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Exceptional
(8 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,898
for 7 nights, 1 apartment
AU$557 per night
includes taxes & fees
Exchange Street Skylight Loft
Interior
Living area
Room
Off-street parking behind building dedicated to this unit only.
Exceptional
(42 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,688
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Outdoor dining
Dining
Interior
Private kitchen
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

8% off
AU$2,713
for 7 nights, 1 apartment
AU$388 per night
includes taxes & fees
Fall In Love With Portland!
Interior
Living area
Private kitchen
Interior
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,203
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Living area
Interior
Dining
Exterior detail
Exceptional
(101 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
AU$2,841
for 7 nights, 1 apartment
AU$406 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Interior
Interior
Walnut topped kitchenette counter with coffee maker.
Living area
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,210
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Large deck with seating for six, festive lighting and a firepit. Views and sun!
5 min car ride to Downtown/Old Port.
Festive lighting at your control.
Mix of nautical and rustic elements throughout.
Exceptional
(132 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

8% off
AU$3,092
for 7 nights, 1 apartment
AU$442 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Exterior detail
Interior
Property grounds
Dining
Exceptional
(21 reviews)

New England Charm, Portland - Parking included

Portland

8% off
AU$4,273
for 7 nights, 1 apartment
AU$610 per night
includes taxes & fees
New England Charm, Portland - Parking included
Living area
Interior
Room
Dining
Exceptional
(22 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,428
for 7 nights, 1 apartment
AU$633 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

  • 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, laundry, 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:

  • 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)
  • Old Orchard Beach Parasail (14.2 mi / 22.8 km)
  • Dunegrass Golf Club (11.2 mi / 18 km)
  • Seacoast Adventure (18 mi / 28.9 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.
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.
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 Stayz.
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.
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.
Are all fees included in the South Portland holiday homes prices shown on Stayz?
Stayz 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.
Are there any South Portland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for South Portland holiday homes?
You can find great discounts on holiday homes in South Portland on Stayz, 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.
Can I change or cancel my South Portland holiday home booking on Stayz?
To find South Portland holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in South Portland?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a South Portland holiday home?
Book your South Portland holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Portland?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in South Portland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas