A lighthouse, rocky coastline, and a sunset over the ocean.

South Portland Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for South Portland vacation rentals

A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (73 reviews)
"Great stay!"
United States
Jason M.
The price is AED 794
AED 1,622 total
includes taxes & fees
30 Nov - 1 Dec
Arlie`s Digs! - One Block To Willard Beach!
A brick wall with a logo and the text 'THE SEND BREWING CO.'

2. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is AED 484
AED 897 total
includes taxes & fees
5 Nov - 6 Nov
Sunny Spot with Private Parking
A brick wall with a logo and the text 'THE SEND BREWING CO.'

3. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AED 504
AED 968 total
includes taxes & fees
5 Nov - 6 Nov
Peaceful & minutes from Old Port w/private parking
A beach with clear water, people swimming, and houses in the background.

4. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
The price is AED 625
AED 1,826 total
includes taxes & fees
17 Nov - 18 Nov
Willard By the Sea - 30 ft to the beach- 2nd floor
A building named Willard Square with a storefront and a red vehicle parked outside.

5. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AED 1,315
AED 2,360 total
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home
A hallway leading to a living room with a sofa, a lamp, and a window.

6. The Coastal Connection by Everrow

The Coastal Connection by Everrow
Thorton Heights
7.2 out of 10, Good, (7 reviews)
"The house was amazing! Close enough to the towns but secluded enough we could truly relax."
United States
Michelle M.
The price is AED 389
AED 1,112 total
includes taxes & fees
2 Dec - 3 Dec
The Coastal Connection by Everrow
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

7. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (129 reviews)
"Really nice room and location"
United States
Victoria
The price is AED 664
AED 999 total
includes taxes & fees
19 Nov - 20 Nov
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

8. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (18 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is AED 900
AED 1,532 total
includes taxes & fees
2 Dec - 3 Dec
Evalina Hotel
A spacious restaurant with wooden tables and benches, large windows, and hanging pendant lights.

9. Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (78 reviews)
"The location is excellent. We were very happy to have onsite parking. The apartment is lovely, nice touches all around. The hosts were easy to work with and quite pleasant. I would definitely recommend the stay."
United States
Linda
The price is AED 1,198
AED 1,850 total
includes taxes & fees
3 Dec - 4 Dec
Historic Home in the West End. Private Parking.
A theater with a marquee reading "STATE" and a classic architectural design.

10. Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.6 out of 10, Exceptional, (24 reviews)
"Super cute apartment that was perfect for our stay in Portland. It was close to Old Port that had lots of cute shops and restaurants."
United States
Erin
The price is AED 661
AED 1,193 total
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo Downtown Portland Old Port
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

11. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is AED 459
AED 769 total
includes taxes & fees
8 Nov - 9 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A bar area with a counter, stools, and a menu board.

12. West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
9.8 out of 10, Exceptional, (30 reviews)
"The space was pristine, comfortable, homey with an excellent location situated to shops and restaurants. Jennifer was a welcoming and warm host and we had no issues at all during our stay!"
United States
Luke E.
The price is AED 731
AED 1,226 total
includes taxes & fees
8 Nov - 9 Nov
West End Bright Spot with Parking.
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

13. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (97 reviews)
"Excellent property in Portland. Clean with amenities needed for any stay. Easy access to downtown. Hosts communicate exceptionally well and property is everything it promotes!"
United States
Adam Y.
The price is AED 356
AED 1,232 total
includes taxes & fees
8 Nov - 9 Nov
Walk to Old Port ♦ West End Condo ♦ Parking
A garden with a stone bridge over a small stream, surrounded by various plants and flowers.

14. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"10/10 would stay again Close to nice bars,restaurants, gas stations. Clean apartment. Host was very nice! "
United States
Mary C.
The price is AED 809
AED 1,459 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
A living room with a sofa, armchairs, a coffee table, and a potted plant.

15. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (34 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AED 303
AED 570 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful 1st Floor Apartment & Amazing Shower
A house with a wooden staircase leading to a door marked with the number 50.

16. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (108 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is AED 435
AED 927 total
includes taxes & fees
8 Nov - 9 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

17. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is AED 303
AED 598 total
includes taxes & fees
10 Nov - 11 Nov
Bright & Spacious Apartment with Amazing Shower
A garden with a stone wall, a small pond, and various plants.

18. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (22 reviews)
"Great house! Wonderful location with so many wonderful touches to make our stay so comfortable. We would definitely stay there again."
United States
Anonymous traveler
The price is AED 1,100
AED 1,823 total
includes taxes & fees
30 Nov - 1 Dec
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

19. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring and visiting Portland! Great communication, easy process, and would definitely stay again if we visit Franklin"
United States
Jordan M.
The price is AED 779
AED 1,283 total
includes taxes & fees
5 Nov - 6 Nov
East end. Walk to food, beer and downtown fun.
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

20. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (11 reviews)
"Great spot. Roomy. Close to shops and ferries. It had everything we needed to see Portland."
United States
Benton M.
The price is AED 726
AED 1,348 total
includes taxes & fees
5 Nov - 6 Nov
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
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
"Good for the price"
Melissa 1-night trip
Posted 2 hours ago
Clarion Hotel Portland Airport ME

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?

Charming 110-year former Inn 10' from the Ocean!: Visitors give good reviews to this South Portland vacation home rental, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in South Portland?

With 26 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 South Portland Historical Society 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 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.