South Portland Vacation Rentals

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Dec 7 - Dec 8
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Dec 19 - Dec 21

Vacation 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)
"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
$180 nightly
The price is $196
Dec 17 - Dec 18
Total with taxes and fees
Sunny Spot with Private Parking.
Interior
The Coastal Connection

The Coastal Connection

2.0 star property
Thorton Heights
$268 nightly
The price is $292
Dec 8 - Dec 9
Total with taxes and fees
The Coastal Connection
Fridge, microwave, oven, stovetop
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.
$417 nightly
The price is $444
Dec 8 - Dec 9
Total with taxes and fees
Modern Getaway by the Sea
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)
"Super Cute little apartment! My only complaint, is the parking. It gets a little tight. And the bed is a little firm for my liking, but overall it was super nice and convenient!"
United States
Samantha
$178 nightly
The price is $194
Dec 8 - Dec 9
Total with taxes and fees
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, (61)
"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.
$283 nightly
The price is $308
Dec 8 - Dec 9
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
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)
"Enjoyed our stay, perfect for 2 kids and parents. Outdoor shower was a great addition for our beach days!"
United States
Greg R.
$535 nightly
The price is $583
Dec 8 - Dec 9
Total with taxes and fees
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
Private kitchen
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

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

South Portland
$575 nightly
The price is $626
Dec 10 - Dec 11
Total with taxes and fees
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

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.
$567 nightly
The price is $618
Dec 8 - Dec 9
Total with taxes and fees
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

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.
$200 nightly
The price is $218
Dec 8 - Dec 9
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Beach
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.
$171 nightly
The price is $186
Dec 8 - Dec 9
Total with taxes and fees
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

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$246 nightly
The price is $262
Dec 14 - Dec 15
Total with taxes and fees
The Weldon Hotel
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, (33)
"Great location and great host. "
United States
Dwight P.
$408 nightly
The price is $445
Dec 8 - Dec 9
Total with taxes and fees
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
$149 nightly
The price is $162
Dec 8 - Dec 9
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Interior
The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage

Freeport
9.8 out of 10, Exceptional, (49)
"Fantastic house in a great location! Will definitely be back"
United States
Brandon G.
The Outlet House, Comfortable Cottage
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
$154 nightly
The price is $156
Dec 8 - Dec 9
Total with taxes and fees
In-town no frills 2 bedroom apt
Smart TV
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.
$145 nightly
The price is $158
Dec 8 - Dec 9
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
Property grounds
Saco/Old Orchard Beach Get Away

Saco/Old Orchard Beach Get Away

2.0 star property
Saco
10.0 out of 10, Exceptional, (3)
"the apartment was perfect! It was clean and comfortable. Bed and pillows were great. Walking distance to some really sweet coffe shops. We fell in love with Swell! Thank you for being so patient with us as navigated some excited kids after long days of playing lacrosse! Great hosts!! "
United States
Jessica L.
$348 nightly
The price is $379
Dec 8 - Dec 9
Total with taxes and fees
Saco/Old Orchard Beach Get Away
Exterior detail
West End Bright Spot with Parking.

West End Bright Spot with Parking.

West End
10.0 out of 10, Exceptional, (16)
"Super cute spot! Wonderful girls weekend!"
United States
Diana M.
$195 nightly
The price is $212
Dec 8 - Dec 9
Total with taxes and fees
West End Bright Spot with Parking.
Fridge, microwave, oven, stovetop
Huge Historic Downtown Townhome

Huge Historic Downtown Townhome

West End
9.8 out of 10, Exceptional, (8)
"We gathered as a family to spend one night in Portland and we could not have been happier with the location. "
United States
Stephen M.
$352 nightly
The price is $383
Dec 8 - Dec 9
Total with taxes and fees
Huge Historic Downtown Townhome
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.
$182 nightly
The price is $198
Jan 4 - Jan 5, 2026
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Clean room, friendly staff, good free breakfast! "
Paige 1-night trip
Posted 1 day ago
Tru by Hilton Portland Airport Area

Find out more about South Portland

Everything you need to know about South Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Portland vacation 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 low season months. For more hustle and bustle, you may prefer to visit South Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Portland rentals

At Expedia, we put the best South Portland vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Quintessential Maine Beach Cottage: You might want to consider this vacation home rental near South Portland, which is located on the beach and has a private yard, a selection of games, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in South Portland?

With 30 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 Bug Light.

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.