South Portland Holiday Rentals

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Holiday Rentals in South Portland

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is AU$425
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

68 East Grand Ave

3.0 star property
Old Orchard Beach
8.6 out of 10, Excellent, (9)
"Across from the beach, close to a lot of activities, the space is up to date and very comfortable , decorated nicely. Outdoor porch area was a nice addition to having extra space. The train does go by very early in the am but that’s not just for this space on the avenue but is something to consider if that bothers you. Communication with Nichole was very easy and she was great to deal with! We loved to space and will definitely stay here again! "
United States
Jeffrey
68 East Grand Ave

Quintessential Maine Beach Cottage

Goose Rocks Beach
10.0 out of 10, Exceptional, (137)
"Absolutely beautiful surroundings and cozy place made for an unforgettable experience! "
United States
Sara S.
Quintessential Maine Beach Cottage

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

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
9.8 out of 10, Exceptional, (124)
"House was beautiful! Comfy beds, amazing views,great location!"
United States
Katherine C.
The Moonglow! A beautiful ocean view house in Biddeford!

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Sebago Lake Cottage on Raymond Cape

Raymond
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

Saco
9.2 out of 10, Wonderful, (15)
"Wonderful stay for a quick visit. Would love to come back and spend more time on the deck and exploring the area. "
United States
Aethena E.
The price is AU$482
includes taxes & fees
11 Nov - 12 Nov
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"Made a great place for a business retreat. WiFi worked well and we had plenty of space to spread out."
United States
dan b.
The price is AU$1,937
includes taxes & fees
16 Nov - 17 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

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

Old Orchard Beach
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Saco
10.0 out of 10, Exceptional, (104)
"Such a beautiful home in an amazing location! "
United States
Michelle H.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

2 min walk to the beach. Pet friendly condo

Old Orchard Beach
8.2 out of 10, Very good, (41)
"Over all it was good, bathroom was off bedroom, not convenient for other guest staying on futon in living room. Backyard for dogs was very small, but enough space for the pups to do their duty. In all it worked for the few days we were there!"
United States
Cindy H.
2 min walk to the beach. Pet friendly condo

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is AU$235
includes taxes & fees
10 Nov - 11 Nov
In-town no frills 2 bedroom apt

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
United States
Anonymous traveller
The price is AU$219
includes taxes & fees
10 Nov - 11 Nov
Studio Unit Walkable Everywhere

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

Old Orchard Beach
9.8 out of 10, Exceptional, (224)
"The view off the deck was breathtaking "
United States
Raymond
The price is AU$535
includes taxes & fees
13 Nov - 14 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Charming cottage with outdoor space, full kitchen, & WiFi - near beach

Goose Rocks Beach
9.4 out of 10, Exceptional, (34)
"Wonderful space for family fun"
United States
Rachel E.
Charming cottage with outdoor space, full kitchen, & WiFi - near beach

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (166)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage

Private Lakefront Estate with 180 Degree Views

Raymond
10.0 out of 10, Exceptional, (7)
"This was a fabulous property in perfect location. The house and grounds were amazing. It was a sensational week."
United States
Brian C.
Private Lakefront Estate with 180 Degree Views

Little Miss Cottages - Two Bedroom Cottage

Old Orchard Beach
9.4 out of 10, Exceptional, (3)
"Cute little cottage. The floor in one bedroom has a real slant to it."
United States
Paula F.
The price is AU$455
includes taxes & fees
10 Nov - 11 Nov
Little Miss Cottages - Two Bedroom Cottage

Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Old Orchard Beach
9.8 out of 10, Exceptional, (44)
"Great house with lots of room for a big family. So close to the beach with great views. Great outdoor spaces as well! "
United States
Moria B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
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$219 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?

Quintessential Maine Beach Cottage: This holiday home rental outside of South Portland is located on the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

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 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.