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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for South Portland vacation rentals

Outdoor dining

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

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
$366 nightly
The price is $399
Sep 4 - Sep 5
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Interior

2. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
$357 nightly
The price is $389
Aug 6 - Aug 7
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
Exterior

3. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
$571 nightly
The price is $604
Aug 23 - Aug 24
Total with taxes and fees
Willard Square Family Home
Outdoor dining

4. Forest City Oasis and Spa

Forest City Oasis and Spa
Pleasantdale
10.0 out of 10, Exceptional, (2 reviews)
"Very charming. It is an apartment on lower floor so there are some upstairs noises but not too bad. The garden is wonderful. Very clean"
United States
Susan M.
$741 nightly
The price is $792
Aug 21 - Aug 22
Total with taxes and fees
Forest City Oasis and Spa
Interior

5. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 reviews)
"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
$298 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Sunny Spot with Private Parking.
Living area

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

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
$1,243 nightly
The price is $1,354
Aug 12 - Aug 13
Total with taxes and fees
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
TV

7. The Coastal Connection

The Coastal Connection
Thorton Heights
7.6 out of 10, Good, (5 reviews)
"Nice clean apartment very updated in older building. 3 Units or so in this renovated house. So expect to hear your neighbors. Also the main road has a lot of traffic at every hour. Semis shake the house. "
United States
Benjamin
$376 nightly
The price is $410
Aug 5 - Aug 6
Total with taxes and fees
The Coastal Connection
Smart TV, fireplace, books

8. 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.
$372 nightly
The price is $406
Aug 24 - Aug 25
Total with taxes and fees
Willard Beach: Cozy Apartment with a King Size Bed
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (107 reviews)
"Really nice room and location"
United States
Victoria
$394 nightly
The price is $423
Aug 31 - Sep 1
Total with taxes and fees
The Weldon Hotel
Interior

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (22 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$289 nightly
The price is $315
Aug 31 - Sep 1
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Beach

11. 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.
$509 nightly
The price is $555
Aug 23 - Aug 24
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

12. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
$359 nightly
The price is $391
Aug 23 - Aug 24
Total with taxes and fees
Fortland Island Campground
Front of property

13. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (7 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$795 nightly
The price is $866
Sep 1 - Sep 2
Total with taxes and fees
Evalina Hotel
TV, fireplace

14. Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (200 reviews)
"We’ve stayed here several times and have had a wonderful experience each time. The property was clean and comfortable and the host was very responsive. Highly recommended!"
United States
Arthur B.
$1,270 nightly
The price is $1,384
Aug 8 - Aug 9
Total with taxes and fees
Waterfront Two Master Suite Penthouse with Rooftop
Smart TV

15. Eastbayside/Munjoy - Charming Downtown Escape

Eastbayside/Munjoy - Charming Downtown Escape
East Bayside
9.8 out of 10, Exceptional, (37 reviews)
"Very nice location, clean and comfortable!"
United States
Ryan R.
$641 nightly
The price is $698
Aug 6 - Aug 7
Total with taxes and fees
Eastbayside/Munjoy - Charming Downtown Escape
Smart TV

16. Newly Renovated 2nd Floor Apt near USM

Newly Renovated 2nd Floor Apt near USM
Oakdale
10.0 out of 10, Exceptional, (17 reviews)
"Per the title great location, cleanliness as advertised."
United States
Edub
$627 nightly
The price is $683
Aug 9 - Aug 10
Total with taxes and fees
Newly Renovated 2nd Floor Apt near USM
Dining

17. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (81 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
$471 nightly
The price is $513
Aug 23 - Aug 24
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
Interior

18. Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (34 reviews)
"Perfect location for walking around the Old Port. Incredible value and exactly what we needed for a weekend away. Would definitely come back. "
United States
Michael M.
$508 nightly
The price is $554
Aug 5 - Aug 6
Total with taxes and fees
Skyline 138: Charming West End Mansard Penthouse
Interior

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (58 reviews)
"Perfect cozy apartment for a get away! Great location that’s walkable for shopping, brunch, and coffee and less than a 15 minute drive from everything else on our itinerary!"
United States
Callie R.
$429 nightly
The price is $468
Aug 10 - Aug 11
Total with taxes and fees
Historic Home in the West End. Private Parking.
Dining

20. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (163 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
$1,131 nightly
The price is $1,233
Aug 6 - Aug 7
Total with taxes and fees
Prime Old Port 3BR • Free Parking • Sleeps 8
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"The facilities were centrally located. It was well maintained. We enjoyed our short stay."
Michael 1-night trip
Posted 6 hours ago
Portland Regency Hotel & Spa

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 $189 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?

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: Visitors like this South Portland vacation home rental. It is located near the beach and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 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 Fort Preble.

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.