South Portland Holiday Rentals

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Our top choices for South Portland holiday rentals

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is AU$263
includes taxes & fees
8 Feb - 9 Feb
Sunny Spot with Private Parking.

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is AU$280
includes taxes & fees
8 Feb - 9 Feb
Peaceful & minutes from the Old Port with private parking

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is AU$538
includes taxes & fees
8 Feb - 9 Feb
Modern Getaway by the Sea

The Coastal Connection

The Coastal Connection
Thorton Heights
The Coastal Connection

Step right out to the beach! Amazing location 7 min to Portland.

Step right out to the beach! Amazing location 7 min to Portland.
Willard
10.0 out of 10, Exceptional, (13 reviews)
"The apartment was very clean and well appointed with everything you might need. The host was very friendly and attentive and check in and check out were very simple. Any questions I had were answered promptly. I would definitely stay here again!"
United States
Diana T.
The price is AU$871
includes taxes & fees
8 Feb - 9 Feb
Step right out to the beach! Amazing location 7 min to Portland.

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
10.0 out of 10, Exceptional, (1 review)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is AU$946
includes taxes & fees
3 Mar - 4 Mar
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AU$775
includes taxes & fees
8 Feb - 9 Feb
Willard Square Family Home

Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.

Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.
Willard
9.6 out of 10, Exceptional, (5 reviews)
"Enjoyed our stay, perfect for 2 kids and parents. Outdoor shower was a great addition for our beach days!"
United States
Greg R.
The price is AU$813
includes taxes & fees
3 Mar - 4 Mar
Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (9 reviews)
"Very private property, was a great little retreat. Such a thoughtfully designed space, and loved being surrounded by nature, including breakfast with deer!"
United States
Dan M.
The price is AU$734
includes taxes & fees
19 Feb - 20 Feb
Cozy Rock Cabin #thewaylifeshouldbe

350 Yards to the beach. Pet friendly!

350 Yards to the beach. Pet friendly!
Old Orchard Beach
8.0 out of 10, Very good, (34 reviews)
"Not as nice as some other places we have stayed in OOB, but for the price and closeness to the beach and pier its great. It is right up against the train tracks which wasn’t horrible for us, but could be a significant problem for a light sleeper. "
United States
Kevin S.
The price is AU$269
includes taxes & fees
2 Mar - 3 Mar
350 Yards to the beach. Pet friendly!

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is AU$313
includes taxes & fees
12 Feb - 13 Feb
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (91 reviews)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$374
includes taxes & fees
17 Feb - 18 Feb
The Weldon Hotel

Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
Adorable 1 bedroom cabin only 50 ft from beach#1

Port City Nest: Beautiful 2bd w/ Balcony & Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking
Parkside
10.0 out of 10, Exceptional, (2 reviews)
"Very nice apartment. Had everything we needed. "
United States
Bob S.
The price is AU$345
includes taxes & fees
8 Feb - 9 Feb
Port City Nest: Beautiful 2bd w/ Balcony & Parking

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is AU$295
includes taxes & fees
11 Feb - 12 Feb
Adorable Portland getaway on the Eastern Promenade

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (27 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AU$229
includes taxes & fees
8 Feb - 9 Feb
Beautiful 1st Floor Apartment & Amazing Shower

West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
10.0 out of 10, Exceptional, (18 reviews)
"Host was clear in arrival instructions and gave great recommendations for places to eat in the neighborhood."
United States
Donna M.
The price is AU$323
includes taxes & fees
8 Feb - 9 Feb
West End Bright Spot with Parking.

Ocean Views and Modern Flair | New Renovation

Ocean Views and Modern Flair | New Renovation
Old Orchard Beach
The price is AU$353
includes taxes & fees
8 Feb - 9 Feb
Ocean Views and Modern Flair | New Renovation

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (37 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is AU$647
includes taxes & fees
8 Feb - 9 Feb
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

4 min walk to the beach. Large 1BD Pets Ok

4 min walk to the beach. Large 1BD Pets Ok
Old Orchard Beach
8.6 out of 10, Excellent, (17 reviews)
"This place is as advertised. Futon was comfortable. Spacious for those who just need a place to sleep/shower after the beach and exploring downtown. Really nothing else to say except pack light if walking to the beach. Overall a good place to stay if you want to explore the area!"
United States
Kate H.
The price is AU$277
includes taxes & fees
9 Feb - 10 Feb
4 min walk to the beach. Large 1BD Pets Ok
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Portland Hotel Reviews

Find out more about South Portland

Everything you need to know about South Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Portland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Portland holiday rentals we have selected for you start as low as AU$180 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Portland rentals

At Expedia, we put the best South Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in South Portland?

Yes, there are holiday rentals close to the most popular sights in South Portland, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in South Portland. Allow some time to check out the waterfront during your trip.

What are some of the best holiday rentals that South Portland has to offer?

Sensational Beachfront Property Old Orchard Beach, with indoor elevator: This holiday home rental outside of South Portland is located on the beach, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in South Portland?

With 29 Expedia holiday rentals, you're guaranteed to find just the right place for your South Portland stay.

What can I see and do in South Portland?

Cultural attractions include Lyric Music Theater and South Portland Historical Society Museum, whereas Willard Beach and Casco Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Maine Mall and Bug Light.

What are holiday rentals like in South Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Portland. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.