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, (111)
"We were two couples (in our 60’s) in Portland for a couple days visiting. John’s place was wonderful! We had plenty of space for the four of us with room to spare. Very comfortable and relaxing. We absolutely LOVED the front porch/deck. Very spacious and an amazing view of the beach and ocean! Bathroom and kitchen were not “updated” but it’s a 110 year old home so we really didn’t mind - everything worked and that’s what’s important. The apartment is upstairs and John lives downstairs. ...
Charming 110-year former Inn 10' from the Ocean!
Quintessential Maine Beach Cottage
10.0 out of 10, Exceptional, (105)
"Great spot, the dog loved it too"
Quintessential Maine Beach Cottage
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)
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
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (99)
"Property was as described, communication was easy and fast, property was clean, spacious, and felt homey. We will be back! "
The price is €508
includes taxes & fees
24 Nov - 25 Nov
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
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
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
9.6 out of 10, Exceptional, (26)
"Repeat visit. Short walk to beach. Convenient to stores if you want to shop. Cottage comfortable. We’ll be back!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
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.
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (122)
"The condo was a little out dated but the balcony and the views of the sunrise can’t be beat!"
The price is €296
includes taxes & fees
25 Nov - 26 Nov
Oceanfront Condo! Spectacular Views From Private Large Balcony
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
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
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
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
9.0 out of 10, Wonderful, (27)
"Cute place - makes very good use of the space. It was comfortable and very conveniently located to everything we wanted to do. We have a few suggestions but overall very happy, had a wonderful time, and the ultimate compliment - we look forward to staying there again. "
The price is €372
includes taxes & fees
23 Nov - 24 Nov
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
9.0 out of 10, Wonderful, (2)
"Our stay at the property was great."
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
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 €295
includes taxes & fees
9 Dec - 10 Dec
Glorious getaway on Portland's Eastern Promenade.
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, (18)
"Close walk to beach restaraunts and pier very nice inside"
NEW TO THE MARKET - 1 block from the 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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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, (2375)
"Good stay "
The price is €74
includes taxes & fees
8 Dec - 9 Dec
Casco Bay Hotel, Ascend Hotel Collection
DoubleTree by Hilton Hotel Portland
4.0 star property
7.8 out of 10, Good, (1030)
"Very nice, but did not always have room cleaned. Out of 6 nights, was cleaned only 3 times. "
The price is €78
includes taxes & fees
2 Dec - 3 Dec
DoubleTree by Hilton Hotel Portland
Comfort Inn Airport
2.5 star property
8.4 out of 10, Very good, (1020)
"Great location! Right down the street from the airport. Nice breakfast, good food. Friendly staff."
The price is €65
includes taxes & fees
5 Dec - 6 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.