Holiday Rentals in South Portland

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Holiday Rentals in South Portland

Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"We loved the location of this property. It was far enough away from the hustle and bustle to truly relax and enjoy the ocean sounds and sunrises, but close enough that we could easily hop on over to shopping and restaurants. The property was well-maintained, we loved the deck, and being able to walk right out on the beach. Highly recommend!"
Charming 110-year former Inn 10' from the Ocean!
Quintessential Maine Beach Cottage
10.0 out of 10, Exceptional, (103)
"Our family took a quick weekend trip to do some birding and enjoy some nature walks. What a great house in an amazing location! We enjoyed sitting in the Adirondack chairs overlooking the marsh every evening as the sun set. The house was absolutely spotless and had everything we needed. It was cozy and comfortable, with plenty of games for entertaining ourselves after dark. It was close to nearby attractions for day trips. The owner was very responsive when we had questions about the heater. We...
Quintessential Maine Beach Cottage
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (95)
"This beach home was clean and beautiful, it had everything we needed and was in a great location. We loved that it was right on the ocean, which meant amazing sun rises and easy access to walks on the beach. We were there in October, so there wasn’t much going on in Old Orchard beach, but that was okay with us! It was a quiet cozy town when we were there. There were plenty of other places to visit in the surrounding area!"
Gorgeous ocean-front home with stunning beach views
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (89)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is €193
includes taxes & fees
11 Nov - 12 Nov
Adorable Portland getaway on the Eastern Promenade
Sensational House on Sebago Lake, Raymond, ME
9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (34)
"Great place. Cool spot. Host was wonderful. Rooftop was awesome. Highly recommend!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (194)
"The sunrises, which we could easily view from the balcony, were spectacular! Music and food from the Swick was also good. The location was great for exploring other areas nearby such as Kennebunkport to Portland. Wendy gave excellent details and gave immediate feedback when needed. "
The price is €324
includes taxes & fees
6 Nov - 7 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (120)
"Great central location for day trips, and then you get relaxing views and sounds of the ocean. There is music from the bar below, but it was a fun atmosphere and we found it enjoyable. "
The price is €301
includes taxes & fees
6 Nov - 7 Nov
Oceanfront Condo! Spectacular Views From Private Large Balcony
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (37)
"Very comfortable. Convenient very easy beach access."
The price is €515
includes taxes & fees
19 Nov - 20 Nov
Beach House ∆ Prime Location ∆ Steps to the Ocean
100 feet from the ocean 3 bedroom cottage 420 friendly
8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is €291
includes taxes & fees
6 Nov - 7 Nov
Glorious getaway on Portland's Eastern Promenade.
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
7.4 out of 10, Good, (26)
"The location was amazing! Walking distance to the pier, and right by the beach! We enjoyed that it was far enough down from the pier that the beach was a bit less crowded but we were still able to walk downtown. The accommodations are very cute and rustic. Some things could use attention, like paint touch ups and the patio table needs replacing… however these were minor issues and we will be back! "
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Beachfront cottage on Fortunes Rocks Beach
10.0 out of 10, Exceptional, (85)
"For anyone who has dreamed of waking up to the sounds of the ocean while watching a spectacular sunrise - this is the place! The house is immaculate and has everything you’ll need! Tyler is awesome and responds to inquiries immediately! We can’t wait to return! "
Beachfront cottage on Fortunes Rocks Beach
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (25)
"We had a wonderful visit to OOB to finish off our summer. The cottage is a quick walk to the beach and pier. It was very clean and comfortable for the four of us to relax and recharge in between swimming, playing mini-gold, and enjoying the amusement park."
The price is €229
includes taxes & fees
3 Dec - 4 Dec
Large 2BD cottage 10 min to Pier & Beach Pets ok
Little Miss Cottages
2.5 star property
8.4 out of 10, Very good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
Little Miss Cottages
2 duplex
3.5 star property
2.0 out of 10, (1)
2 duplex
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
8.2 out of 10, Very good, (12)
"We enjoyed our brief stay"
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
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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Other types of properties in South Portland you may be interested in

Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.4 out of 10, Very good, (2340)
"We enjoyed the staying."
The price is €79
includes taxes & fees
19 Nov - 20 Nov
Casco Bay Hotel, Ascend Hotel Collection
Days Inn by Wyndham Airport/Maine Mall
2.0 star property
7.8 out of 10, Good, (1001)
"Free breakfast "
The price is €89
includes taxes & fees
6 Nov - 7 Nov
Days Inn by Wyndham Airport/Maine Mall
Comfort Inn Airport
2.5 star property
8.4 out of 10, Very good, (1000)
"Was a quick overnight stay at the start of our vacation. Quick check in and clean hotel"
The price is €63
includes taxes & fees
2 Dec - 3 Dec
Comfort Inn Airport
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.

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?

Charming 110-year former Inn 10' from the Ocean!: This highly rated holiday home rental in South Portland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in South Portland?

With 49 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.