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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for South Portland vacation rentals

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

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.
$301 nightly
The price is $329
Sep 7 - Sep 8
Total with taxes and fees
The Coastal Connection
A dining table with chairs, a potted plant, and decorative items.

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.
$305 nightly
The price is $332
Sep 16 - Sep 17
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A building named Willard Square with a storefront and a red vehicle parked outside.

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.
$686 nightly
The price is $730
Sep 14 - Sep 15
Total with taxes and fees
Willard Square Family Home
A beach with a wooden chair and a small building in the background.

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.
$786 nightly
The price is $857
Oct 1 - Oct 2
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
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.

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.
$318 nightly
The price is $347
Sep 29 - Sep 30
Total with taxes and fees
Willard Beach: Cozy Apartment with a King Size Bed
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

6. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (116 reviews)
"Really nice room and location"
United States
Victoria
$395 nightly
The price is $431
Sep 7 - Sep 8
Total with taxes and fees
The Weldon Hotel
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

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.
$165 nightly
The price is $166
Sep 7 - Sep 8
Total with taxes and fees
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)
"Lovely home in a beautiful location and Dan is a fantastic host. Ask him about his hot sauce!"
United States
Elliott H.
$423 nightly
The price is $461
Sep 6 - Sep 7
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A gym with treadmills, elliptical machines, and exercise balls.

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, (11 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
$164 nightly
The price is $178
Sep 7 - Sep 8
Total with taxes and fees
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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
$270 nightly
The price is $294
Oct 5 - Oct 6
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
A modern living room with a sofa, a coffee table, a TV, and a window with blinds.

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)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
$292 nightly
The price is $318
Sep 18 - Sep 19
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
A snow-covered landscape with a house and a tree.

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.
$277 nightly
The price is $302
Sep 7 - Sep 8
Total with taxes and fees
Serenity between the lakes and seashore
A spacious living room with a large window, a fireplace, and a view of a marina.

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)
"This was one of the most spectacular places we have ever stayed. The views are amazing and the place is just incredible. We really look forward to our next visit!"
United States
Daryl R.
$1,057 nightly
The price is $1,152
Sep 27 - Sep 28
Total with taxes and fees
Penthouse Two Master Waterfront Suite with Rooftop
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

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.
$541 nightly
The price is $589
Sep 7 - Sep 8
Total with taxes and fees
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.
$605 nightly
The price is $659
Sep 13 - Sep 14
Total with taxes and fees
Newly Renovated 2nd Floor Apt near USM
A two-story house with a balcony, a covered patio, and a fenced yard.

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.
$522 nightly
The price is $569
Sep 15 - Sep 16
Total with taxes and fees
The Globe House on Munjoy Hill - Walk to Breweries
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

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.
$348 nightly
The price is $371
Sep 8 - Sep 9
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
A modern apartment with a living room, dining area, and kitchen.

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.
$555 nightly
The price is $605
Sep 7 - Sep 8
Total with taxes and fees
2 Bedroom Apartment on Top Floor in Portland's West End
A beach with a sunset, a pier, and a building with 'erly' on it.

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
$309 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
4 min Walk to Pier & Beach. Center of OOB FREE Pk
A wooden bench on a rocky shore overlooking a calm body of water.

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.
$394 nightly
The price is $429
Sep 15 - Sep 16
Total with taxes and fees
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

Best Western Merry Manor Inn

Best Western Merry Manor Inn

10/10 Excellent
"The Merry Manor is conveniently located near airport and downtown. We stayed twice, once in a room that was ok and then got a nicer room when we returned. We liked that the shower and toilet were in a separate room with a sink and then an exterior sink accommodated the other person. There was a coffee maker, microwave and fridge with plenty of room for 2 suitcases. The breakfast was varied and surprisingly good for a motel. We used the hot tub and discovered that the pool is slightly heated as well, so a swim in cool weather was pleasant. All told, we enjoyed our stay."
Gail Swick 2-night trip
Posted 13 hours ago
Best Western Merry Manor Inn

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 $178 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?

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.