South Portland Vacation Rentals

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Our top choices for South Portland vacation rentals

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 $413
CA $702 total
includes taxes & fees
Mar 27 - Mar 28
Modern Getaway by the Sea

The Coastal Connection

The Coastal Connection
Thorton Heights
The price is CA $146
CA $438 total
includes taxes & fees
Mar 29 - Mar 30
The Coastal Connection

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 $133
CA $276 total
includes taxes & fees
Mar 29 - Mar 30
Sunny Spot with Private Parking.

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 $205
CA $596 total
includes taxes & fees
Mar 29 - Mar 30
Step right out to the beach! Amazing location 7 min to Portland.

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 $365
CA $773 total
includes taxes & fees
Mar 31 - Apr 1
Willard Square Family Home

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 CA $175
CA $347 total
includes taxes & fees
Apr 5 - Apr 6
Peaceful & minutes from the Old Port with private parking

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 CA $301
CA $504 total
includes taxes & fees
Apr 5 - Apr 6
Toast to 2026! Free Champagne for all Jan / Feb Bookings

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 $205
CA $596 total
includes taxes & fees
Mar 29 - Mar 30
Ocean views 30 Steps to Beach! Amazing,walkable location 7 min to Portland.

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.6 out of 10, Exceptional, (9 reviews)
"The room was spotless. The hotel was very clean and the staff was very friendly and helpful."
United States
Monique
The price is CA $130
CA $142 total
includes taxes & fees
Apr 11 - Apr 12
HomeAwhile

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 CA $205
CA $545 total
includes taxes & fees
Mar 29 - Mar 30
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (26 reviews)
"Great place. Had everything we needed and close to everything."
United States
Bill P.
The price is CA $196
CA $502 total
includes taxes & fees
Mar 30 - Mar 31
Skyline 138: Charming West End Mansard Penthouse

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.4 out of 10, Exceptional, (99 reviews)
"Great location with easy parking"
United States
Lauren J.
The price is CA $143
CA $358 total
includes taxes & fees
Apr 2 - Apr 3
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (54 reviews)
"Host was very welcoming and the place exceeded expectations! Made our stay better than we could have imagined!"
United States
Robert D.
The price is CA $197
CA $372 total
includes taxes & fees
Mar 29 - Mar 30
Historic Home in the West End. Private Parking.

Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.4 out of 10, Very good, (18 reviews)
"Super cute. Enjoyed our stay"
United States
Amber T.
The price is CA $112
CA $235 total
includes taxes & fees
Mar 29 - Mar 30
Bright & Spacious Apartment with Amazing Shower

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 CA $211
CA $478 total
includes taxes & fees
Mar 31 - Apr 1
State of Charm | Historic West End Haven

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 CA $173
CA $642 total
includes taxes & fees
Mar 29 - Mar 30
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Prime Location.Private Rooftop Deck.Walk to Old Port,Waterfront, Museum & Music

Prime Location.Private Rooftop Deck.Walk to Old Port,Waterfront, Museum & Music
Downtown Portland
9.2 out of 10, Wonderful, (28 reviews)
"Cozy apartment, close to everything! We walked to Batson River, Congress Street, and the Old Port. Also loved Gill's, right across the street!"
United States
Kimberley J.
The price is CA $246
CA $650 total
includes taxes & fees
Mar 31 - Apr 1
Prime Location.Private Rooftop Deck.Walk to Old Port,Waterfront, Museum & Music

Prime Central West End spacious 3BR.Walk to Waterfront,Old Port & music venues

Prime Central West End spacious 3BR.Walk to Waterfront,Old Port & music venues
West End
10.0 out of 10, Exceptional, (17 reviews)
"Great location with a well set up layout!"
United States
Airynn M.
The price is CA $939
CA $1,766 total
includes taxes & fees
Mar 29 - Mar 30
Prime Central West End spacious 3BR.Walk to Waterfront,Old Port & music venues

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (172 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is CA $201
CA $386 total
includes taxes & fees
Mar 29 - Mar 30
Glorious getaway on Portland's Eastern Promenade.

Brand New 1 Bedroom Apartment in Portland

Brand New 1 Bedroom Apartment in Portland
West End
10.0 out of 10, Exceptional, (45 reviews)
"Great host communication, super clean and good location!"
United States
Lorraine V.
The price is CA $233
CA $528 total
includes taxes & fees
Mar 29 - Mar 30
Brand New 1 Bedroom Apartment in 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.
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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?

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 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.