South Portland Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for South Portland vacation rentals

Interior

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 ￥17,116
￥33,986 total
includes taxes & fees
Apr 1 - Apr 2
Sunny Spot with Private Parking.
TV

The Coastal Connection

The Coastal Connection
Thorton Heights
The price is ￥13,808
￥47,103 total
includes taxes & fees
Apr 1 - Apr 2
The Coastal Connection
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (8 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 ￥20,296
￥38,671 total
includes taxes & fees
Apr 5 - Apr 6
Peaceful & minutes from the Old Port with private parking
Microwave, oven, stovetop, dishwasher

Toast to 2026! Free Champagne for all Jan / Feb Bookings

Toast to 2026! Free Champagne for all Jan / Feb Bookings
South Portland
10.0 out of 10, Exceptional, (4 reviews)
"The house was very nice and had great accommodations for our group. The kitchen and living room was very accommodating for meals and hangouts and we were close to all of the activities we were looking to do"
United States
Justin R.
The price is ￥67,919
￥99,464 total
includes taxes & fees
Apr 5 - Apr 6
Toast to 2026! Free Champagne for all Jan / Feb Bookings
Interior

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 ￥47,943
￥81,190 total
includes taxes & fees
Apr 1 - Apr 2
Modern Getaway by the Sea
On the beach, sun loungers, beach towels

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 ￥23,812
￥68,981 total
includes taxes & fees
Apr 1 - Apr 2
Step right out to the beach! Amazing location 7 min to Portland.
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home
On the beach, sun loungers, beach towels

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)
"Our host was available and helpful, everything clean and great location"
United States
Janet H.
The price is ￥31,802
￥78,561 total
includes taxes & fees
Apr 13 - Apr 14
Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.
Desk, laptop workspace, free WiFi

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.6 out of 10, Exceptional, (13 reviews)
"The room was spotless. The hotel was very clean and the staff was very friendly and helpful."
United States
Monique
The price is ￥16,780
￥18,290 total
includes taxes & fees
Apr 1 - Apr 2
HomeAwhile
Dining

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.4 out of 10, Exceptional, (3 reviews)
"All was great...clean and convenient."
United States
Krista P.
The price is ￥20,199
￥74,438 total
includes taxes & fees
Apr 1 - Apr 2
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
Fridge, microwave, oven, stovetop

Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (19 reviews)
"Wonderful stay! Place was amazing and host is very responsive. Thank you so much "
United States
Logan R.
The price is ￥13,009
￥27,245 total
includes taxes & fees
Apr 5 - Apr 6
Bright & Spacious Apartment with Amazing Shower
Outdoor dining

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 ￥19,976
￥44,593 total
includes taxes & fees
Apr 1 - Apr 2
Port City Nest: Beautiful 2bd w/ Balcony & Parking
Dining

Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (49 reviews)
"Great stay in the heart of Portland, the bathtub was so good for a warming soak after a cool day of exploring the arts district! The host was very accommodating and we will be considering staying here again, for sure! "
United States
James S.
The price is ￥21,327
￥38,227 total
includes taxes & fees
Apr 1 - Apr 2
Charming West End Hideaway. Private Parking
Outdoor dining

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is ￥32,505
￥52,328 total
includes taxes & fees
Apr 5 - Apr 6
Modern, Luxurious, Cabin in the Woods - 17
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is ￥40,272
￥62,013 total
includes taxes & fees
Apr 1 - Apr 2
Large, luxurious geodesic dome - 04
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is ￥10,068
￥21,542 total
includes taxes & fees
Apr 1 - Apr 2
Private Entrance Residential Portland
Interior

State of Charm | Historic West End Haven

State of Charm | Historic West End Haven
Parkside
9.0 out of 10, Wonderful, (12 reviews)
"Great for our family trip!"
United States
Sonya M.
The price is ￥26,407
￥57,525 total
includes taxes & fees
Apr 14 - Apr 15
State of Charm | Historic West End Haven
Interior

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is ￥16,444
￥60,427 total
includes taxes & fees
Apr 15 - Apr 16
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (7 reviews)
"Maine Oyster Company was a highlight of the trip! "
United Kingdom
Tyler P.
The price is ￥12,585
￥24,059 total
includes taxes & fees
Apr 15 - Apr 16
Studio Apartment near downtown Walkable!
Dining

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Downtown Portland
9.6 out of 10, Exceptional, (22 reviews)
"A great location for exploring the city. The apartment was clean and comfortable. The coffee shop across the street was an added perk! "
United States
abbey b.
The price is ￥26,512
￥66,698 total
includes taxes & fees
Apr 6 - Apr 7
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern 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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Top South Portland Hotel Reviews

Home2 Suites by Hilton Portland Airport

Home2 Suites by Hilton Portland Airport

10/10 Excellent
"Clean Room"
Sherri 1-night trip
Posted 1 hour ago
Home2 Suites by Hilton Portland Airport

Find out more about South Portland

Search for holiday rentals in South Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in South Portland using one of the methods below:

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Look no further and take a look at our great range of rental properties in South Portland!

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?

Beach House ∆ Prime Location ∆ Steps to the Ocean: Visitors like this South Portland vacation home rental. It is located on the waterfront and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in South Portland?

With 28 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 Fort Preble.

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.