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

South Portland Vacation Rentals

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Our top choices for South Portland vacation rentals

1. The Coastal Connection

The Coastal Connection
Thorton Heights
7.0 out of 10, Good, (6 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is CA $155
CA $448 total
includes taxes & fees
Sep 8 - Sep 9
The Coastal Connection

2. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Excellent in every way."
United States
Robert B.
The price is CA $209
CA $454 total
includes taxes & fees
Sep 16 - Sep 17
Willard Beach–Apartment Near Portland & Parks

3. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is CA $553
CA $1,010 total
includes taxes & fees
Sep 14 - Sep 15
Willard Square Family Home

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is CA $744
CA $1,209 total
includes taxes & fees
Oct 1 - Oct 2
Arlie`s Digs! - One Block To Willard Beach!

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

Willard Beach: Cozy Apartment with a King Size Bed
Willard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Lovely and quiet. Just what I had hoped for. "
United States
Heather R.
The price is CA $214
CA $467 total
includes taxes & fees
Sep 21 - Sep 22
Willard Beach: Cozy Apartment with a King Size Bed

6. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (117 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $525
CA $676 total
includes taxes & fees
Sep 21 - Sep 22
The Weldon Hotel

7. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (11 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is CA $131
CA $230 total
includes taxes & fees
Sep 8 - Sep 9
Private Entrance Residential Portland

8. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is CA $415
CA $641 total
includes taxes & fees
Sep 14 - Sep 15
Ocean View East End Studio in a Historic Victorian

9. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.0 out of 10, Wonderful, (13 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is CA $199
CA $247 total
includes taxes & fees
Sep 8 - Sep 9
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

10. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (27 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is CA $248
CA $409 total
includes taxes & fees
Oct 5 - Oct 6
Charming Studio apartment with WiFi, AC in welcoming Portland

11. Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (40 reviews)
"Great vacation rental. Convenient to all we wanted to do in the area. Very clean and very livable property!"
United States
Thomas M.
The price is CA $242
CA $436 total
includes taxes & fees
Sep 18 - Sep 19
Pine Point Beach private, quaint, charming studio.

12. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
Serenity between the lakes and seashore

13. Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (268 reviews)
Penthouse Two Master Waterfront Suite with Rooftop

14. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

15. Newly Renovated 2nd Floor Apt near USM

Newly Renovated 2nd Floor Apt near USM
Oakdale
10.0 out of 10, Exceptional, (17 reviews)
"Property is very nice, in a nice location, easy to walk to various stores/locations. It was well stocked with all the basics we would need."
United States
mary m.
The price is CA $663
CA $912 total
includes taxes & fees
Sep 14 - Sep 15
Newly Renovated 2nd Floor Apt near USM

16. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is CA $443
CA $820 total
includes taxes & fees
Sep 15 - Sep 16
The Globe House on Munjoy Hill - Walk to Breweries

17. 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, (42 reviews)
"Exactly as described and in one of the loveliest parts of Portland! Communication with owner was smooth and seamless. Perfect place to get to multiple places of interest in this charming city."
United States
Emily W.
The price is CA $295
CA $511 total
includes taxes & fees
Sep 8 - Sep 9
East end. Walk to food, beer and downtown fun.

18. 2 Bedroom Apartment on Top Floor in Portland's West End

2 Bedroom Apartment on Top Floor in Portland's West End
West End
10.0 out of 10, Exceptional, (85 reviews)
"Lovely stay at a lovely place!"
United States
Bunny B.
The price is CA $483
CA $836 total
includes taxes & fees
Sep 8 - Sep 9
2 Bedroom Apartment on Top Floor in Portland's West End

19. 4 min Walk to Pier & Beach. Center of OOB FREE Pk

4 min Walk to Pier & Beach. Center of OOB FREE Pk
Old Orchard Beach
9.4 out of 10, Exceptional, (27 reviews)
"Great location, clean, easy access. "
United States
Jean Anthony
The price is CA $160
CA $425 total
includes taxes & fees
Sep 8 - Sep 9
4 min Walk to Pier & Beach. Center of OOB FREE Pk

20. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is CA $342
CA $592 total
includes taxes & fees
Sep 15 - Sep 16
City Amenities, Casco Bay Sunrises and Natural Beauty
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

Find out more about South Portland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Portland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 28 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.