South Portland Holiday Rentals

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Our top choices for South Portland holiday 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 AU$724
includes taxes & fees
26 Mar - 27 Mar
Modern Getaway by the Sea

The Coastal Connection

The Coastal Connection
Thorton Heights
The price is AU$467
includes taxes & fees
29 Mar - 30 Mar
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 AU$289
includes taxes & fees
30 Mar - 31 Mar
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 AU$601
includes taxes & fees
26 Mar - 27 Mar
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 AU$792
includes taxes & fees
26 Mar - 27 Mar
Willard Square Family Home

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 AU$353
includes taxes & fees
5 Apr - 6 Apr
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 AU$868
includes taxes & fees
5 Apr - 6 Apr
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 AU$608
includes taxes & fees
7 Apr - 8 Apr
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, (8 reviews)
"Staff fabulous, very clean"
United States
Verronika
The price is AU$148
includes taxes & fees
26 Mar - 27 Mar
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 AU$543
includes taxes & fees
26 Mar - 27 Mar
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 AU$475
includes taxes & fees
26 Mar - 27 Mar
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 AU$364
includes taxes & fees
7 Apr - 8 Apr
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, (52 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 AU$384
includes taxes & fees
29 Mar - 30 Mar
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 AU$207
includes taxes & fees
26 Mar - 27 Mar
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 AU$454
includes taxes & fees
26 Mar - 27 Mar
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 AU$649
includes taxes & fees
29 Mar - 30 Mar
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 AU$660
includes taxes & fees
31 Mar - 1 Apr
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.
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 AU$361
includes taxes & fees
26 Mar - 27 Mar
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.
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

Everything you need to know about South Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Portland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Portland holiday rentals we have selected for you start as low as AU$148 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Portland rentals

At Expedia, we put the best South Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beach House ∆ Prime Location ∆ Steps to the Ocean: This holiday home rental outside of South Portland is located on the waterfront, and has a balcony, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in South Portland?

With 28 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.