South Portland Vacation Rentals from ￥23,344: Search Short-Term Rentals

Q: 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.

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Our top choices for South Portland vacation rentals

A modern living room with a grey sofa, a small glass table, and a woven rug. There is a kitchen area with a white countertop and hanging lights.

1. Willard Beach: Cozy Apartment with a King Size Bed

Willard Beach

Heather R.

￥47,957 total

includes taxes & fees

Oct 29 - Oct 30

A black console table with a mirror above it, a lamp, and a potted plant beside it.

2. Peaceful & minutes from the Old Port with private parking

Knightville

Kelly S.

￥52,803 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

3. Sunny Spot with Private Parking.

Knightville

Irish D.

￥51,595 total

includes taxes & fees

Oct 19 - Oct 20

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

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

Willard Beach

Melissa M.

￥69,418 total

includes taxes & fees

Nov 9 - Nov 10

A hallway leading to a living room with a sofa, a lamp, and a window.

5. The Coastal Connection

Thorton Heights

Sheryl S.

￥49,083 total

includes taxes & fees

Nov 9 - Nov 10

A building named Willard Square with a storefront and a red vehicle parked outside.

6. Willard Square Family Home

Willard Beach

David W.

￥89,483 total

includes taxes & fees

Oct 14 - Oct 15

A coastal view with a house, a tree, and a beach.

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

Willard

"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."

Gerald B.

￥93,032 total

includes taxes & fees

Nov 9 - Nov 10

A dining table with chairs, a potted plant, and decorative items.

8. Willard Beach–Apartment Near Portland & Parks

Willard Beach

Linda

￥49,696 total

includes taxes & fees

Oct 25 - Oct 26

A beach with clear water, people swimming, and houses in the background.

9. Willard By the Sea - 30 ft to the beach

Willard

Gerald B.

￥88,959 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

10. The Weldon Hotel

Downtown Portland

Victoria

￥45,621 total

includes taxes & fees

Nov 2 - Nov 3

A multi-story building with a stone facade, large windows, and a corner entrance.

11. Evalina Hotel

Downtown Portland

Rick

￥75,288 total

includes taxes & fees

Nov 10 - Nov 11

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

12. Studio Apartment near downtown Walkable!

West Bayside

Lucy T.

￥23,834 total

includes taxes & fees

Nov 4 - Nov 5

A living room with a sofa, armchairs, a coffee table, and a potted plant.

13. Beautiful 1st Floor Apartment & Amazing Shower

Parkside

Jocelyn R.

￥28,971 total

includes taxes & fees

Nov 9 - Nov 10

A house with a wooden staircase leading to a door marked with the number 50.

14. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

West End

Gary

￥42,864 total

includes taxes & fees

Nov 4 - Nov 5

A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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

Munjoy Hill

Aimee S.

￥36,410 total

includes taxes & fees

Nov 1 - Nov 2

A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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

West End

Adam Y.

￥59,688 total

includes taxes & fees

Nov 1 - Nov 2

A narrow pathway leading to a wooden house with a porch, surrounded by lush greenery and trees.

17. King Size Bed - West End Studio - Walk to Old Port

West End

￥36,590 total

includes taxes & fees

Nov 2 - Nov 3

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

18. Great suburban location close to town!

Deering Center

Peter H.

￥15,324 total

includes taxes & fees

Oct 25 - Oct 26

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

￥61,629 total

includes taxes & fees

Oct 20 - Oct 21

A modern house with a wooden exterior, a small garden, and a visible window.

20. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

East Bayside

Mallory D.

￥74,632 total

includes taxes & fees

Oct 19 - Oct 20

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Top South Portland Hotel Reviews

Fireside Inn & Suites Portland

10/10 Excellent

"Everything was clean and well maintained. Rustic charm We like the fact that the hot tub cool and so on were open till 11:00 p.m. And the grab and go breakfast was also available until 11:00 a.m. which is nice because when you're on vacation you sometimes keep odd hours and it's nice when there are services available."

Clarion Hotel Portland Airport ME

8/10 Good

"I stayed here for a conference in town because it was convenient and the price was so much more reasonable than the ridiculous situation going on in the Old Port. I can’t believe people are truly willing to spend +500$ a night to stay in a city in Maine in a Monday, but that’s what it’s come to. My roommate worked at the Clarion when I lived in Portland over 20 years ago, and I don’t think it’s changed much, although I don’t know if the name was the same. The rooms are perfectly nice, they’ve probably been updated in the last ten years, with comfortable beds and a bathroom that’s not fabulous, but also not really any worse than more expensive fancier hotels where I’ve stayed, just with less modern decor. My only complaint is basically accessibility. The parking is not necessarily going to get you anywhere near the entrance that’s convenient to your room and there’s only one elevator it the back of the lobby. It’s quite tiny and a bit rickety, and my room was a literal haul from where the elevator stopped on my floor. I had a bunch of bags and there wasn’t a cart in sight, not that I think one would have fit in the elevator, now that I’m thinking of it. Overall I would definitely recommend it for people who don’t mind a short drive into town (they do have a shuttle service) and want to save their money for everything else Portland has to offer besides outrageously priced lodging."

Clarion Pointe South Portland

8/10 Good

"I really enjoyed our stay and the bonus of being away from the city! It’s convenient to get to and from Portland/the highway systems! I just wish there were two nightstand tables instead of one so we could’ve plugged in our phones easier. The king room seemed to be set up for one person in mind. Otherwise it was pretty easy and great with welcoming staff!"

Find out more about South Portland

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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.

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Check prices for these dates

Our top choices for South Portland vacation rentals

1. Willard Beach: Cozy Apartment with a King Size Bed

2. Peaceful & minutes from the Old Port with private parking

3. Sunny Spot with Private Parking.

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

5. The Coastal Connection

6. Willard Square Family Home

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

8. Willard Beach–Apartment Near Portland & Parks

9. Willard By the Sea - 30 ft to the beach

10. The Weldon Hotel

11. Evalina Hotel

12. Studio Apartment near downtown Walkable!

13. Beautiful 1st Floor Apartment & Amazing Shower

14. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

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

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

17. King Size Bed - West End Studio - Walk to Old Port

18. Great suburban location close to town!

19. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

20. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Find vacation rentals that suit your style

Top South Portland Hotel Reviews

Fireside Inn & Suites Portland

Tru by Hilton Portland Airport Area

The Westin Portland Harborview

Clarion Hotel Portland Airport ME

Spark by Hilton Portland Airport Maine Mall

Clarion Pointe South Portland

TownePlace Suites by Marriott Portland Airport ME

DoubleTree by Hilton Hotel Portland

Best Western Merry Manor Inn

Find out more about South Portland

Frequently asked questions

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