South Portland Holiday Rentals

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Our top choices for South Portland holiday 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 AU$322
includes taxes & fees
10 May - 11 May
Sunny Spot with Private Parking.

The Coastal Connection

The Coastal Connection
Thorton Heights
The price is AU$417
includes taxes & fees
10 May - 11 May
The Coastal Connection

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, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is AU$344
includes taxes & fees
10 May - 11 May
Peaceful & minutes from the Old Port with private parking

Willard Beach–Private Apt Near Portland & Parks

Willard Beach–Private Apt Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is AU$356
includes taxes & fees
14 May - 15 May
Willard Beach–Private Apt Near Portland & Parks

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
The price is AU$298
includes taxes & fees
10 May - 11 May
South Portland Beach area rental

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$574
includes taxes & fees
12 May - 13 May
Arlie`s Digs! - One Block To Willard Beach!

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is AU$742
includes taxes & fees
13 May - 14 May
Modern Getaway by the Sea

Willard Beach: Cozy Apartment with a King Size Bed

Willard Beach: Cozy Apartment with a King Size Bed
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Lovely and quiet. Just what I had hoped for. "
United States
Heather R.
The price is AU$473
includes taxes & fees
26 May - 27 May
Willard Beach: Cozy Apartment with a King Size Bed

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.
The price is AU$1,030
includes taxes & fees
19 May - 20 May
Willard Square Family Home

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (10 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 AU$816
includes taxes & fees
11 May - 12 May
Cozy Rock Cabin #thewaylifeshouldbe

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is AU$569
includes taxes & fees
7 June - 8 June
Fortland Island Campground

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 AU$498
includes taxes & fees
13 May - 14 May
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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 AU$264
includes taxes & fees
10 May - 11 May
Beautiful 1st Floor Apartment & Amazing Shower

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is AU$337
includes taxes & fees
10 May - 11 May
Modern, Luxurious Cabin in the Woods - 03

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$357
includes taxes & fees
26 May - 27 May
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (38 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is AU$427
includes taxes & fees
10 May - 11 May
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is AU$314
includes taxes & fees
13 May - 14 May
Charming Studio apartment with WiFi, AC in welcoming Portland

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
10.0 out of 10, Exceptional, (1 review)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is AU$223
includes taxes & fees
13 May - 14 May
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (56 reviews)
"This place is amazing. Another wonderful few days spent in a cozy place with everything you need. "
United States
Tom B.
The price is AU$387
includes taxes & fees
10 May - 11 May
Historic Home in the West End. Private Parking.

NEW TO THE MARKET - 1 block from the beach!

NEW TO THE MARKET - 1 block from the beach!
Old Orchard Beach
10.0 out of 10, Exceptional, (28 reviews)
"Close to the beach which is what we were looking for."
United States
Terrence S.
The price is AU$344
includes taxes & fees
21 May - 22 May
NEW TO THE MARKET - 1 block from the beach!
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$291 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?

The Lookout by Bayley Vacation Rentals: This holiday home rental outside of South Portland is located by the ocean, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 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 27 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.