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Top Holiday Rentals in South Portland

Our top choices for South Portland holiday rentals

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (72)
"Absolutely beautiful place to stay. "
The price is £266
includes taxes & fees
1 Sept - 2 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 £415
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, (17)
"Stunning property and great location! "
The price is £524
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
8.0 out of 10, Very good, (7)
"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 £1,653
includes taxes & fees
5 Sept - 6 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.

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 £261
includes taxes & fees
24 Aug - 25 Aug
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 £444
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 £376
includes taxes & fees
10 Sept - 11 Sept
Oceanfront Condo! Spectacular Views From Private Large Balcony

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

9.8 out of 10, Exceptional, (126)
"Right on the beach. Beautiful view. Clean and well appointed apartment Would definitely recommend and return "
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

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

9.6 out of 10, Exceptional, (55)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is £225
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 £218
includes taxes & fees
8 Sept - 9 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

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

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

9.4 out of 10, Exceptional, (9)
The price is £189
includes taxes & fees
26 Aug - 27 Aug
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
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

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.