South Portland Holiday Rentals

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Holiday Rentals in South Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (76)
"Absolutely beautiful place to stay. "
The price is AU$814
includes taxes & fees
8 Sept - 9 Sept
The Weldon Hotel

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (217)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (75)
"Wonderful spot with great accommodations! Would definitely stay again!"
Grand Victorian on the Beach, Summer

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (63)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
The price is AU$2,242
includes taxes & fees
8 Sept - 9 Sept
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Bright and airy condo with beachfront access and walkable entertainment nearby

8.0 out of 10, Very good, (1)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (20)
"Stunning property and great location! "
The price is AU$871
includes taxes & fees
3 Sept - 4 Sept
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"Second time staying hear. Will continue to repeat"
Gorgeous ocean-front home with stunning beach views

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (225)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

10.0 out of 10, Exceptional, (4)
"Very clean and comfortable, we enjoyed our stay."
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.6 out of 10, Excellent, (12)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (45)
"Great location. House was clean. "
The price is AU$843
includes taxes & fees
15 Sept - 16 Sept
Beach House ∆ Prime Location ∆ Steps to the Ocean

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (88)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (138)
"Great place. Perfect location if you want to be in the middle of it all."
The price is AU$712
includes taxes & fees
15 Sept - 16 Sept
Oceanfront Condo! Spectacular Views From Private Large Balcony

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (36)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Luxury apartment near Old Orchard Beach

10.0 out of 10, Exceptional, (3)
"Very nice apartment, very clean."
The price is AU$382
includes taxes & fees
15 Sept - 16 Sept
Luxury apartment near Old Orchard Beach

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
The price is AU$675
includes taxes & fees
4 Sept - 5 Sept
350 Yards to the beach. Pet friendly!

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (126)
"This unit surpassed our expectations. Excellent location, the unit was impeccable, had everything we needed and more.Highly recommend renting from Owner.. I know we will be!"
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
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

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$382 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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of South Portland is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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 a selection of games.

How many holiday rentals are there in South Portland?

With 30 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 Bug Light and Maine Mall.

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.