South Portland holiday homes

We found 471 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:20 Nov - 27 Nov

Interior
Interior
Private kitchen
Pool
Exceptional
(17 reviews)

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

Scarborough

8% off
NZ$6,779
for 7 nights, 1 home
NZ$968 per night
includes taxes & fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Room
Terrace/patio
Private kitchen
Interior
Wonderful
(23 reviews)

Beautiful, single story ranch. Next to city park with ocean view!

Portland

8% off
NZ$10,749
for 7 nights, 1 home
NZ$1,536 per night
includes taxes & fees
Beautiful, single story ranch. Next to city park with ocean view!
Exterior detail
Outdoor dining
Private kitchen
The living room leads out to a private deck with a dining table that seats 4.
Exceptional
(42 reviews)

Modern & Sunny House Steps from the Promenade. Private Parking!

Portland

8% off
NZ$4,851
for 7 nights, 1 home
NZ$693 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade. Private Parking!
Kitchen
Master Bedroom
View from Master Bedroom
Living area
Exceptional
(33 reviews)

Amazing Oceanfront Brand NewHome Ideal location -

Peaks Island

8% off
NZ$9,262
for 7 nights, 1 home
NZ$1,323 per night
includes taxes & fees
Amazing Oceanfront Brand NewHome Ideal location -
Private kitchen
Interior
Dining
Interior
Exceptional
(31 reviews)

Sunny Spot with Private Parking.

South Portland

8% off
NZ$2,643
for 7 nights, 1 apartment
NZ$378 per night
includes taxes & fees
Sunny Spot with Private Parking.
Living area
Marina
Private kitchen
Living area
Exceptional
(13 reviews)

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

South Portland

16% off
NZ$3,072
for 7 nights, 1 apartment
NZ$439 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
View from inside unit.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Massive 100 inch smart TV
Exceptional
(6 reviews)

Exchange Street Skylight Loft

Portland

8% off
NZ$4,138
for 7 nights, 1 apartment
NZ$591 per night
includes taxes & fees
Exchange Street Skylight Loft
Private kitchen
Living area
Interior
Dining
Exceptional
(133 reviews)

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

Portland

12% off
NZ$3,571
for 7 nights, 1 apartment
NZ$510 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Private kitchen
Outdoor dining
Interior
Living area
Exceptional
(11 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
NZ$2,613
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Dining
Interior
Living area
Exterior detail
Exceptional
(99 reviews)

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

Portland

8% off
NZ$3,417
for 7 nights, 1 apartment
NZ$488 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Room
Scales in the Old Port for the best seafood
Interior
Discover Victoria Mansion at the bottom of the street.
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
NZ$3,261
for 7 nights, 1 apartment
NZ$466 per night
includes taxes & fees
Charming West End Hideaway. Private Parking
Baharat, across the street from rising tide.
Minato is a quick walk away.
View from the top of the Portland Observatory.
Living area
Exceptional
(140 reviews)

Adorable Portland getaway on the Eastern Promenade

Portland

12% off
NZ$1,643
for 7 nights, 1 apartment
NZ$235 per night
includes taxes & fees
Adorable Portland getaway on the Eastern Promenade
Room
Interior
Interior
Living area
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
NZ$5,206
for 7 nights, 1 apartment
NZ$744 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Large, well-stocked Kitchen w/stainless steel counter and appliances
5 min car ride to Downtown/Old Port.
Large deck with seating for six, festive lighting and a firepit. Views and sun!
Festive lighting at your control.
Exceptional
(131 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

6% off
NZ$3,756
for 7 nights, 1 apartment
NZ$537 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior
Interior
Living area
Dining
Exceptional
(20 reviews)

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

Portland

8% off
NZ$5,476
for 7 nights, 1 apartment
NZ$782 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)
  • 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)

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 home?
Willard is one of the more in-demand neighbourhoods to book a holiday home in South Portland. Spend your getaway here to delight in the privacy and comfort that comes with having a whole place to yourself.
What is the most popular type of holiday home accommodation in South Portland?
According to our research, houses are the most popular property type in South Portland. But as you'd expect, everyone's idea of an awesome trip is bound to be different. Bookabach has holiday homes of all shapes and sizes, so you're sure to find the perfect match.
How much does it cost to rent a holiday home in South Portland?
The average price for a holiday home in South Portland is determined by several factors, like season, property type and length of stay. Whether you're searching for a sprawling villa with space for extended family or a quaint cottage for you and your other half, just enter your travel dates to view stays with unbeatable value.
How much does it cost to rent a beach house in South Portland?
Prices for beach houses in South Portland can vary depending on the size and type of the property and time of year you're travelling. Simply enter your dates of travel into Bookabach and the number of guests to view your holiday home options and prices. From there you can use the filters to narrow your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in South Portland?
With 41 holiday homes that welcome pets, your furry friend can join in on your South Portland break. Use our filter tool to search our pet-friendly holiday homes and find a stay that'll set tails wagging on Bookabach.
Can I rent a house with a pool in South Portland?
Add another level of fun to your adventure by staying in one of the 16 houses with a private pool in South Portland. Use our search filter to find properties with pools on Bookabach, then spend lazy days splish-splashing around in a swimming pool that's exclusively for you.
What are popular home amenities in South Portland?
When it comes to home amenities that guests are on the lookout for in South Portland, a swimming pool, a nearby waterfront and tennis rank highest. With Bookabach holiday homes, you'll enjoy options to fit your taste and style, whether you're travelling with family, friends or even pets.
Are there large group holiday homes in South Portland?
Choose from six holiday homes in South Portland that can accommodate 10 or more people. Whether you're planning a get-together with extended family or a special event, there's enough room to get your loved ones together under one roof.
Are there holiday homes in South Portland that welcome kids?
South Portland has 41 family-friendly holiday homes. And securing a stay that welcomes children is a cinch with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll get conveniences and perks such as bunk beds, yards and private pools.
What are the top attractions for families in South Portland?
Keeping the kiddos entertained during your stay in South Portland is simple with these fabulous family-friendly attractions:
  • Higgins Beach
  • East End Beach
  • Pine Point Beach
Are there one-bedroom holiday homes in South Portland?
You can pick from 15 one-bedroom homes in South Portland. Whether you're searching for a comfy cottage or a cabin, Bookabach's one-bedroom properties are perfect if you don't need a lot of space. One of the perks of having your own pad? You won't need to share your getaway with strangers.
Can I find two-bedroom holiday homes in South Portland?
Select from nine two-bedroom homes in South Portland. Give your little ones the second room or fill it with a couple of your besties. There's a comfy spot for whoever's fortunate enough to be joining your journey.
Are there holiday homes with WiFi in South Portland?
There are 11 holiday homes with WiFi in South Portland. If you'd like to disconnect from the world while on holiday, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in South Portland?
Decide on your travel dates and then make use of our filters to see holiday homes with air conditioning in South Portland on Bookabach. With 36 air-conditioned properties available, you can look forward to a cool and comfy break.
How old do you have to be to rent a holiday home in South Portland?
The minimum age is typically 16, 18 or 21. It can vary from property to property on Bookabach, so look at the rules of your preferred South Portland stay before making a booking.
How long can I rent a holiday home in South Portland for?
The amount of time you can rent a South Portland holiday home for is down to each property. Just tap in your dates of travel to find available options offering extended stays. They have all you need to make your extended holiday more comfortable like laundries and air conditioning. Some holiday homes might also offer discounted weekly or monthly prices, so you can stay longer for less money.