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, (75)
"Absolutely beautiful place to stay. "
The price is NZ$769
includes taxes & fees
2 Sept - 3 Sept
The Weldon Hotel

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

9.8 out of 10, Exceptional, (215)
"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. "
The price is NZ$932
includes taxes & fees
1 Sept - 2 Sept
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

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

10.0 out of 10, Exceptional, (18)
"Stunning property and great location! "
The price is NZ$965
includes taxes & fees
1 Sept - 2 Sept
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Great location. "
68 East Grand Ave

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

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 NZ$2,765
includes taxes & fees
8 Sept - 9 Sept
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages

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.

Beach across the Street. Pets OK

8.6 out of 10, Excellent, (30)
"Perfect spot! Right near the beach and walking distance to all the best places. Very clean and chill little place perfect for what I was going for."
Beach across the Street. Pets OK

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 NZ$756
includes taxes & fees
8 Sept - 9 Sept
350 Yards to the beach. Pet friendly!

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

10.0 out of 10, Exceptional, (224)
"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

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (45)
"Great location. House was clean. "
The price is NZ$970
includes taxes & fees
15 Sept - 16 Sept
Beach House ∆ Prime Location ∆ Steps to the Ocean

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (137)
"Great place. Perfect location if you want to be in the middle of it all."
The price is NZ$788
includes taxes & fees
15 Sept - 16 Sept
Oceanfront Condo! Spectacular Views From Private Large Balcony

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.6 out of 10, Excellent, (11)
"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

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)

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (56)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is NZ$516
includes taxes & fees
14 Sept - 15 Sept
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

2 min walk to the beach. Pet friendly condo

8.0 out of 10, Very good, (37)
"Host was very accommodating and easy to contact & communicate with. I'll definitely stay again! Highly recommended "
The price is NZ$427
includes taxes & fees
9 Sept - 10 Sept
2 min walk to the beach. Pet friendly condo

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

10.0 out of 10, Exceptional, (2)
"A beautiful home, very clean, and a perfect location for us. Short walking distance to everything we wanted to do. "
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach
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 favorite 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 depends 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 NZ$427 per night. Entering your travel dates in the search wizard you might find 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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This holiday home rental outside of South Portland offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in South Portland?

With 57 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.