South Portland Holiday Rentals

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Our top choices for South Portland holiday rentals

The Coastal Connection

The Coastal Connection
Thorton Heights
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is NZ$548
includes taxes & fees
10 June - 11 June
The Coastal Connection

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 NZ$1,027
includes taxes & fees
14 June - 15 June
Arlie`s Digs! - One Block To Willard Beach!

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, just like pictures "
United States
Evan M.
The price is NZ$515
includes taxes & fees
10 June - 11 June
South Portland Beach area rental

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 NZ$546
includes taxes & fees
11 June - 12 June
Willard Beach–Private Apt Near Portland & Parks

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 NZ$1,024
includes taxes & fees
11 June - 12 June
Willard Square Family Home

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (26 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 NZ$459
includes taxes & fees
11 June - 12 June
Sunny Spot with Private Parking.

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

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
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 NZ$1,643
includes taxes & fees
18 June - 19 June
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (11 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 NZ$1,115
includes taxes & fees
10 June - 11 June
Cozy Rock Cabin #thewaylifeshouldbe

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (2 reviews)
"Spacious, clean, and in the perfect location in Old Port."
United States
Celine
The price is NZ$1,030
includes taxes & fees
15 June - 16 June
Evalina Hotel

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (176 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is NZ$529
includes taxes & fees
10 June - 11 June
Glorious getaway on Portland's Eastern Promenade.

'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
'osprey Cottage' South Freeport Home on Casco Bay!

Completely remodeled 2 bedroom apartment in Portland's West End

Completely remodeled 2 bedroom apartment in Portland's West End
West End
10.0 out of 10, Exceptional, (78 reviews)
"Had a great time exploring Maine. Close to restaurants and "
United States
Megan N.
The price is NZ$865
includes taxes & fees
10 June - 11 June
Completely remodeled 2 bedroom apartment in Portland's West End

Little Miss Cottages - One Bedroom Cottage

Little Miss Cottages - One Bedroom Cottage
Old Orchard Beach
9.6 out of 10, Exceptional, (4 reviews)
"It was very clean and it’s pet friendly. The host went above and beyond and was truly friendly while doing so. A great location and quiet at this time of year. The bed was very comfortable. The shower nice and hot. I would rent that seaside shanty again. "
United States
Lynne B.
The price is NZ$530
includes taxes & fees
10 June - 11 June
Little Miss Cottages - One Bedroom Cottage

NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (4 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is NZ$720
includes taxes & fees
10 June - 11 June
NEW 1 BDR-Heart of Munjoy Hill

Bright & Sunny West End Apartment with Private Parking.

Bright & Sunny West End Apartment with Private Parking.
West End
10.0 out of 10, Exceptional, (51 reviews)
"LOCATION, SUPER CLEAN & BRIGHT - LOVED OUR STAY!"
United States
JODY H.
The price is NZ$835
includes taxes & fees
22 June - 23 June
Bright & Sunny West End Apartment with Private Parking.

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 NZ$306
includes taxes & fees
14 June - 15 June
Studio Apartment near downtown Walkable!

Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (28 reviews)
"Perfect place for our family to rest and be together near the hospital. Very clean and comfortable "
United States
Hilary J.
The price is NZ$630
includes taxes & fees
10 June - 11 June
Skyline 138: Charming West End Mansard Penthouse

Old Port Penthouse Suite - Amazing Harbor Views

Old Port Penthouse Suite - Amazing Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (251 reviews)
"We loved our stay and will definitely book again the next time we come to Portland. The location is perfect - right in the middle of restaurants and just a short block’s walk to Fore St. for shopping. We loved the relaxing design of the apartment, and the views did not disappoint. Can’t wait to go back!"
United States
Barbara K.
The price is NZ$1,572
includes taxes & fees
10 June - 11 June
Old Port Penthouse Suite - Amazing Harbor Views

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$816
includes taxes & fees
10 June - 11 June
Modern & Sunny House Steps from the Promenade. Private Parking!

Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (102 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is NZ$797
includes taxes & fees
28 June - 29 June
Ocean View East End Studio in a Historic Victorian
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 favorite 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 depends 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 NZ$306 per night. Entering your travel dates in the search wizard you might find 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?

Modern, Spacious Guest Suite Near the Ocean: This holiday home rental outside of South Portland is located on the beach, and has a patio, a garden and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and an electric kettle. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in South Portland?

With 29 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 Maine Military Museum and Lyric Music Theater, 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.