South Portland Holiday Rentals

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Check prices for these dates

Tonight
7 Nov - 8 Nov
Tomorrow
8 Nov - 9 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in South Portland

Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
The price is HK$723
HK$1,517 total
includes taxes & fees
9 Nov - 10 Nov
Sunny Spot with Private Parking.
Outdoor dining
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)
"My husband and I had a wonderful weekend in South Portland and enjoyed the central location and charming touches of Jennifer’s apartment. The space is lovely, exactly as described in the listing. The communication was clear and detailed. We will definitely return!"
United States
Caitlin C.
The price is HK$762
HK$1,678 total
includes taxes & fees
13 Nov - 14 Nov
Peaceful & minutes from the Old Port with private parking
Beach nearby
Arlie`s Digs! - One Block To Willard Beach!

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

Willard Beach
10.0 out of 10, Exceptional, (60)
"Near beach, walking, bakery, ice cream and close to great restaurants. Lovely spot and easily accommodated 2 couples. Would stay here again!"
United States
Kirstin D.
The price is HK$1,360
HK$3,008 total
includes taxes & fees
17 Nov - 18 Nov
Arlie`s Digs! - One Block To Willard Beach!
Private kitchen
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

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

Cash Corner
The price is HK$1,431
HK$4,653 total
includes taxes & fees
8 Dec - 9 Dec
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Fridge, microwave, oven, stovetop
Modern Getaway by the Sea

Modern Getaway by the Sea

Cash Corner
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is HK$2,721
HK$3,799 total
includes taxes & fees
15 Nov - 16 Nov
Modern Getaway by the Sea
On the beach, sun-loungers, beach towels
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2

Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2

Willard
9.6 out of 10, Exceptional, (4)
"I cannot say enough about the location! Our two families rented the upstairs and downstairs units, and were very happy with our stay. Great communication with the owner, well-appointed, comfortable beds. Would definitely stay here again. "
United States
Julie W.
The price is HK$2,130
HK$4,534 total
includes taxes & fees
9 Nov - 10 Nov
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
On the beach, sun-loungers, beach towels
Step right out to the beach! Amazing location 7 min to Portland. Unit 4

Step right out to the beach! Amazing location 7 min to Portland. Unit 4

Willard
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay. It was comfortable and clean. Cute decor and right by a great beach. Would stay there again and recommend it to others."
United States
Millicent W.
The price is HK$2,130
HK$4,593 total
includes taxes & fees
19 Nov - 20 Nov
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower

Parkside
9.0 out of 10, Wonderful, (25)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is HK$505
HK$1,186 total
includes taxes & fees
11 Nov - 12 Nov
Beautiful 1st Floor Apartment & Amazing Shower
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is HK$754
HK$1,458 total
includes taxes & fees
9 Nov - 10 Nov
Adorable Portland getaway on the Eastern Promenade
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Old Orchard Beach
8.0 out of 10, Very good, (24)
"Cozy little cotrage"
United States
craig H.
The price is HK$777
HK$1,695 total
includes taxes & fees
10 Nov - 11 Nov
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Property grounds
Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"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 HK$902
HK$1,805 total
includes taxes & fees
2 Dec - 3 Dec
Modern, Luxurious Cabin in the Woods - 03
Beach nearby
Escape to the Beach! Cozy Condo in downtown OOB.

Escape to the Beach! Cozy Condo in downtown OOB.

Old Orchard Beach
9.6 out of 10, Exceptional, (26)
"Super convenient location!"
United States
Bethany T.
The price is HK$661
HK$1,551 total
includes taxes & fees
24 Nov - 25 Nov
Escape to the Beach! Cozy Condo in downtown OOB.
Interior
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Old Orchard Beach
10.0 out of 10, Exceptional, (31)
"Great location and great host. "
United States
Dwight P.
The price is HK$1,547
HK$3,458 total
includes taxes & fees
10 Nov - 11 Nov
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Property grounds
Welcome to our BoHo Treehouse!

Welcome to our BoHo Treehouse!

2.0 star property
Saco
10.0 out of 10, Exceptional, (8)
"Minutes from baseball fields in Biddeford. Clean room which was very nice and beautiful backyard oasis. Very comfortable and nicely decorated. Hot tub which came in handy after long days of games. Would highly recommend. "
United States
Robert F.
The price is HK$809
HK$1,975 total
includes taxes & fees
16 Nov - 17 Nov
Welcome to our BoHo Treehouse!
Beach nearby
Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1

Old Orchard Beach
10.0 out of 10, Exceptional, (3)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
The price is HK$1,081
HK$1,830 total
includes taxes & fees
17 Nov - 18 Nov
Adorable 1 bedroom cabin only 50 ft from beach#1
Interior
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Harpswell
10.0 out of 10, Exceptional, (4)
"Beautiful location!! Very comfortable and clean home "
United States
Beth L.
The price is HK$1,406
HK$4,424 total
includes taxes & fees
7 Dec - 8 Dec
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Interior
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Saco
10.0 out of 10, Exceptional, (13)
"perfect for a couple wanting something that is clean and cozy near beaches in Maine"
United States
Karalyn K.
The price is HK$865
HK$2,291 total
includes taxes & fees
13 Nov - 14 Nov
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Interior
Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking

West End
10.0 out of 10, Exceptional, (45)
"Great apartment in an excellent location. Super walkable to most of Portland. We loved the charming decor and outdoor deck! Furnishings and fixtures were a bit dated and we encountered a few issues with bugs getting in, likely because of the window AC unit. Location felt very safe and hosts were kind."
United States
Ansley D.
The price is HK$987
HK$1,788 total
includes taxes & fees
9 Nov - 10 Nov
Charming West End Hideaway. Private Parking
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Old Orchard Beach
9.8 out of 10, Exceptional, (223)
"Great location."
United States
donna S.
The price is HK$1,361
HK$2,636 total
includes taxes & fees
8 Nov - 9 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Beach nearby, sun-loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay the weekend after Christmas. The home had absolutely everything we needed and was both comfortable and beautiful! Everything was clearly labeled and so easy settle in. Very close to the beach which was awesome to visit even in the winter!"
United States
Elizabeth M.
The price is HK$1,102
HK$3,633 total
includes taxes & fees
8 Nov - 9 Nov
Beach House ∆ Prime Location ∆ Steps to the Ocean
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Great hotel, no issues "
Sam 4-night trip
Posted 2 days ago
Portland Regency Hotel & Spa

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:

  • View our selection of featured holiday rentals in South Portland
  • Use the map to find apartments and other holiday homes in the South Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Portland while they last

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

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?

Quintessential Maine Beach Cottage: This holiday home rental outside of South Portland is located on the beach, and has a private garden, 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 full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

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 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 Bug Light and Maine Mall.

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.