South Portland Vacation Rentals

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Our top choices for South Portland vacation rentals

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is CA $113
CA $250 total
includes taxes & fees
Feb 8 - Feb 9
Sunny Spot with Private Parking.

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is CA $114
CA $267 total
includes taxes & fees
Feb 8 - Feb 9
Peaceful & minutes from the Old Port with private parking

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is CA $274
CA $528 total
includes taxes & fees
Feb 8 - Feb 9
Modern Getaway by the Sea

The Coastal Connection

The Coastal Connection
Thorton Heights
The Coastal Connection

Step right out to the beach! Amazing location 7 min to Portland.

Step right out to the beach! Amazing location 7 min to Portland.
Willard
10.0 out of 10, Exceptional, (13 reviews)
"The apartment was very clean and well appointed with everything you might need. The host was very friendly and attentive and check in and check out were very simple. Any questions I had were answered promptly. I would definitely stay here again!"
United States
Diana T.
The price is CA $405
CA $841 total
includes taxes & fees
Feb 8 - Feb 9
Step right out to the beach! Amazing location 7 min to Portland.

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
10.0 out of 10, Exceptional, (1 review)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is CA $358
CA $955 total
includes taxes & fees
Mar 2 - Mar 3
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is CA $349
CA $748 total
includes taxes & fees
Feb 8 - Feb 9
Willard Square Family Home

Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.

Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.
Willard
9.6 out of 10, Exceptional, (5 reviews)
"Enjoyed our stay, perfect for 2 kids and parents. Outdoor shower was a great addition for our beach days!"
United States
Greg R.
The price is CA $375
CA $808 total
includes taxes & fees
Feb 10 - Feb 11
Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (9 reviews)
"Very private property, was a great little retreat. Such a thoughtfully designed space, and loved being surrounded by nature, including breakfast with deer!"
United States
Dan M.
The price is CA $376
CA $721 total
includes taxes & fees
Feb 19 - Feb 20
Cozy Rock Cabin #thewaylifeshouldbe

350 Yards to the beach. Pet friendly!

350 Yards to the beach. Pet friendly!
Old Orchard Beach
8.0 out of 10, Very good, (34 reviews)
"Not as nice as some other places we have stayed in OOB, but for the price and closeness to the beach and pier its great. It is right up against the train tracks which wasn’t horrible for us, but could be a significant problem for a light sleeper. "
United States
Kevin S.
The price is CA $96
CA $255 total
includes taxes & fees
Mar 2 - Mar 3
350 Yards to the beach. Pet friendly!

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is CA $137
CA $298 total
includes taxes & fees
Feb 18 - Feb 19
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (91 reviews)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is CA $230
CA $354 total
includes taxes & fees
Mar 10 - Mar 11
The Weldon Hotel

Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
The price is CA $149
CA $311 total
includes taxes & fees
Feb 8 - Feb 9
Adorable 1 bedroom cabin only 50 ft from beach#1

Port City Nest: Beautiful 2bd w/ Balcony & Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking
Parkside
10.0 out of 10, Exceptional, (2 reviews)
"Very nice apartment. Had everything we needed. "
United States
Bob S.
The price is CA $116
CA $329 total
includes taxes & fees
Feb 8 - Feb 9
Port City Nest: Beautiful 2bd w/ Balcony & Parking

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is CA $151
CA $279 total
includes taxes & fees
Feb 9 - Feb 10
Adorable Portland getaway on the Eastern Promenade

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (27 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is CA $104
CA $225 total
includes taxes & fees
Feb 8 - Feb 9
Beautiful 1st Floor Apartment & Amazing Shower

West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
10.0 out of 10, Exceptional, (18 reviews)
"Host was clear in arrival instructions and gave great recommendations for places to eat in the neighborhood."
United States
Donna M.
The price is CA $141
CA $308 total
includes taxes & fees
Feb 8 - Feb 9
West End Bright Spot with Parking.

Ocean Views and Modern Flair | New Renovation

Ocean Views and Modern Flair | New Renovation
Old Orchard Beach
The price is CA $115
CA $354 total
includes taxes & fees
Feb 8 - Feb 9
Ocean Views and Modern Flair | New Renovation

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (37 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is CA $182
CA $636 total
includes taxes & fees
Feb 8 - Feb 9
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

4 min walk to the beach. Large 1BD Pets Ok

4 min walk to the beach. Large 1BD Pets Ok
Old Orchard Beach
8.6 out of 10, Excellent, (17 reviews)
"This place is as advertised. Futon was comfortable. Spacious for those who just need a place to sleep/shower after the beach and exploring downtown. Really nothing else to say except pack light if walking to the beach. Overall a good place to stay if you want to explore the area!"
United States
Kate H.
The price is CA $103
CA $264 total
includes taxes & fees
Feb 9 - Feb 10
4 min walk to the beach. Large 1BD Pets Ok
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Portland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in South Portland?

Yes, you can find vacation rentals close to the most popular sights in South Portland, or you can choose a more secluded option if you'd like a relaxing place to 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 vacation home rentals in South Portland?

Sensational Beachfront Property Old Orchard Beach, with indoor elevator: You might want to consider this vacation home rental near South Portland, which is located on the beach and has a balcony, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in South Portland?

With 29 Expedia vacation rentals, you're sure 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 vacation rentals like in South Portland?

Vacation rentals are private properties you can reserve for several days or longer in South Portland. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.