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South Portland Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for South Portland vacation rentals

Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (25)
"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 ￥15,187
￥31,401 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7)
"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 ￥15,344
￥33,620 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (63)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is ￥21,644
￥52,604 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Arlie`s Digs! - One Block To Willard Beach!
Fridge, microwave, oven, stovetop
Modern Getaway by the Sea

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is ￥39,143
￥69,987 total
includes taxes & fees
Dec 30 - Dec 31
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

Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
Willard
9.6 out of 10, Exceptional, (5)
"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 ￥42,900
￥91,133 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
Interior
The Coastal Connection

The Coastal Connection

The Coastal Connection
2.0 star property
Thorton Heights
The price is ￥19,784
￥52,795 total
includes taxes & fees
Dec 30 - Dec 31
The Coastal Connection
Property grounds
Willard Square Family Home

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed this house! "
United States
David W.
The price is ￥36,794
￥80,976 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Willard Square Family Home
Private kitchen
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

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

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
The price is ￥35,228
￥102,226 total
includes taxes & fees
Jan 5 - Jan 6, 2026
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
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

Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Willard
10.0 out of 10, Exceptional, (13)
"Great area, close to the beach, water views, close to Portland, and everything in the apartment worked really well. There has been a lot of attention paid as to what would make a guest's stay really awesome. "
United States
David F.
The price is ￥46,345
￥95,229 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
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

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very Good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is ￥15,657
￥33,279 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Beach nearby
Adorable 1 bedroom cabin only 50 ft from beach#1

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 ￥17,066
￥31,060 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Adorable 1 bedroom cabin only 50 ft from beach#1
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128)
"The place was perfect. It was right in the middle of everything and a perfe spot for a getaway"
United States
Jon S.
The price is ￥17,223
￥31,914 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Adorable Portland getaway on the Eastern Promenade
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is ￥11,023
￥24,815 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Beautiful 1st Floor Apartment & Amazing Shower
Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
2.0 star property
Blue Point
10.0 out of 10, Exceptional, (25)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is ￥12,526
￥31,231 total
includes taxes & fees
Dec 30 - Dec 31
Pine Point Beach private, quaint, charming studio.
Beach nearby
Escape to the Beach! Cozy Condo in downtown OOB.

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)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
The price is ￥14,091
￥31,572 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Escape to the Beach! Cozy Condo in downtown OOB.
1 bedroom, WiFi, bed sheets
Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is ￥9,864
￥21,106 total
includes taxes & fees
Dec 30 - Dec 31
Studio Apartment near downtown Walkable!
Beach
350 Yards to the beach. Pet friendly!

350 Yards to the beach. Pet friendly!

350 Yards to the beach. Pet friendly!
Old Orchard Beach
8.0 out of 10, Very Good, (34)
"Not as nice as some other places we have stayed in OOB, but for the price and closeness to the beach and pier its great. It is right up against the train tracks which wasn’t horrible for us, but could be a significant problem for a light sleeper. "
United States
Kevin S.
The price is ￥10,960
￥29,183 total
includes taxes & fees
Jan 21 - Jan 22, 2026
350 Yards to the beach. Pet friendly!
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is ￥34,728
￥37,854 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Weldon Hotel
Exterior detail
West End Bright Spot with Parking.

West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
10.0 out of 10, Exceptional, (17)
"Great location, clean with everything we needed. Will definitely stay again when in Portland!"
United States
vanessa h.
The price is ￥17,849
￥37,204 total
includes taxes & fees
Jan 11 - Jan 12, 2026
West End Bright Spot with Parking.
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt
West Bayside
8.6 out of 10, Excellent, (17)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is ￥13,152
￥24,394 total
includes taxes & fees
Jan 1 - Jan 2, 2026
In-town no frills 2 bedroom apt
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"The airport shuttle was very convenient and appreciated on an early and snowy Christmas Eve morning. Night and morning desk staff were very helpful and friendly. "
Pattie 1-night trip
Posted 3 days ago
Clarion Hotel Portland Airport ME

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 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?

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families! : You might want to consider this vacation home rental near South Portland, which is located in the city center and has a patio, a garden, 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. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in South Portland?

With 31 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 Fort Preble.

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.