South Portland Holiday Rentals

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Holiday Rentals in South Portland

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (100)
"The view and location are amazing. The house was very comfortable for the three adults on our trip. It’s also very suitable for a family with kids as one of the rooms has two bunk bed sets. It’s comfortable, cozy, and completely relaxing. Within walking distance of the pier and entertainment. Great place to stay. "
Gorgeous ocean-front home with stunning beach views

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (100)
"So happy that I did not pass this one up...the home was gorgeous, comfortable, close to the water, and exactly what was listed. Nick was very responsive, honest, and answered my many questions. Our family's first visit to Portland to celebrate with my daughter for her white coat ceremony at UNE was one to remember. From waking up early to get some Holy Donuts, cheering on the local hockey team, meeting a wonderful florist, walking next to the ocean, and having an owl in the tree right outside...
The price is AU$837
includes taxes & fees
19 Dec - 20 Dec
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (38)
"The house is very clean, and it is only a minute walk to the beach. This was the second time we’ve stayed in this house and it won’t be the last! "
The price is AU$784
includes taxes & fees
22 Dec - 23 Dec
Beach House ∆ Prime Location ∆ Steps to the Ocean

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

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

9.8 out of 10, Exceptional, (195)
"My family had a wonderful stay at your condo. They had unbelievably nice weather and got to enjoy your deck and views in early Nov. "
The price is AU$541
includes taxes & fees
20 Dec - 21 Dec
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

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, (118)
"Clean, comfortable and quiet! Beautiful views of ocean."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

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

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

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

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

Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach

7.4 out of 10, Good, (11)
"House was clean. The trash in the yard was over turned and spilling everywhere when we got there and there was a ton of it but it was picked up within 2 hours of us being there. Comfy house, cute. We couldn’t use the back deck there are holes in the deck covered by carpets. Great location overall we had a great family vacation with two families."
Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach

Sea View Escape #23|Steps to the beach|Recently Updated| Bayley Vacation Rentals

9.4 out of 10, Exceptional, (24)
"Close to the beach, smaller but just want our family needed for a family getaway!!!! Great place, clean, perfect!!!"
Sea View Escape #23|Steps to the beach|Recently Updated| Bayley Vacation Rentals

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

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

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!

2 duplex

3.5 star property
2.0 out of 10, (1)
2 duplex

Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub

9.0 out of 10, Wonderful, (20)
"Celebrating (2) of my closest friends 40th birthday and we stayed at this lovely home! Great setup for a larger group - plenty of room for everyone! Jason was absolutely wonderful communicating with from start to finish and would definitely recommended! The kitchen drawers, cabinets and broom closet could use some cleaning & organizing and the overall was very clean and accommodating! The hot tub was broken upon arrival and Jason did a great job of communicating. We were only there for the one...
The price is AU$1,146
includes taxes & fees
7 Jan - 8 Jan 2025
Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub

2 min walk to the beach. Pet friendly condo

8.2 out of 10, Very good, (31)
"Nice and clean inside. The exterior needs TLC. Great spot."
2 min walk to the beach. Pet friendly condo
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, (2407)
"Fantastic place for the price. The location is at Maine Mall. Friendly staff and decent bfast. Excellent value. "
The price is AU$136
includes taxes & fees
31 Dec - 1 Jan 2025
Casco Bay Hotel, Ascend Hotel Collection

Tru by Hilton Portland Airport Area

2.5 star property
9.0 out of 10, Wonderful, (1232)
"The lobby area was very well laid out as their food court, in the round, where the complimentary breakfast is served. Clean, neat, and kept tidy by staff people.pleasing array of plentiful tasty items and brought fresh when needed. The middle floor round.about was all sorts of foods,drinks, and multiple frozen meals at additional cost. A bit pricie, but if you just don't want to go out for a meal, a decent selection s a great option. A nice easy programable microwave is there as well. Ice...
The price is AU$138
includes taxes & fees
1 Jan - 2 Jan 2025
Tru by Hilton Portland Airport Area

DoubleTree by Hilton Hotel Portland

4.0 star property
7.8 out of 10, Good, (1051)
"I needed a room close to PWM for an early morning flight and for the price it was clean safe and convenient with a shuttle. The property is a little bit “tired” but the staff was really nice from check-in to checkout as well as shuttle driver"
The price is AU$129
includes taxes & fees
2 Jan - 3 Jan 2025
DoubleTree by Hilton Hotel Portland
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 Fort Preble.

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.