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. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (11 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$368 nightly
The price is $401
Sep 1 - Sep 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking

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.
$345 nightly
The price is $376
Sep 16 - Sep 17
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks

3. 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
$300 nightly
The price is $327
Sep 1 - Sep 2
Total with taxes and fees
Sunny Spot with Private Parking.

4. 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
$364 nightly
The price is $397
Sep 7 - Sep 8
Total with taxes and fees
The Coastal Connection

5. 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

6. Forest City Oasis and Spa

Forest City Oasis and Spa
Pleasantdale
10.0 out of 10, Exceptional, (4 reviews)
"Spacious apartment with lovely patio and gardens."
United States
Kathryn S.
$753 nightly
The price is $805
Aug 21 - Aug 22
Total with taxes and fees
Forest City Oasis and Spa

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (68 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$625 nightly
The price is $681
Sep 7 - Sep 8
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!

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.
$342 nightly
The price is $373
Sep 2 - Sep 3
Total with taxes and fees
Willard Beach: Cozy Apartment with a King Size Bed

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (110 reviews)
"Really nice room and location"
United States
Victoria
$369 nightly
The price is $396
Sep 1 - Sep 2
Total with taxes and fees
The Weldon Hotel

10. 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.
$1,467 nightly
The price is $1,599
Aug 28 - Aug 29
Total with taxes and fees
Waterfront Two Master Suite Penthouse with Rooftop

11. Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (267 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.
$1,611 nightly
The price is $1,756
Aug 29 - Aug 30
Total with taxes and fees
Penthouse Two Master Waterfront Suite with Rooftop

12. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (105 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
$239 nightly
The price is $260
Aug 31 - Sep 1
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

13. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$683 nightly
The price is $744
Aug 31 - Sep 1
Total with taxes and fees
Evalina Hotel

14. Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (235 reviews)
"Amazing property and location. Perfect to explore the old port."
United States
Kevin P.
$1,176 nightly
The price is $1,282
Aug 27 - Aug 28
Total with taxes and fees
Downtown Penthouse Suite - Stunning Harbor Views

15. Incredible Location! Heart of Old Port/Spacious Apartment

Incredible Location! Heart of Old Port/Spacious Apartment
Downtown Portland
10.0 out of 10, Exceptional, (45 reviews)
"Great stay, beautiful place and perfect location. "
United States
Heather P.
$1,017 nightly
The price is $1,109
Aug 17 - Aug 18
Total with taxes and fees
Incredible Location! Heart of Old Port/Spacious Apartment

16. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (61 reviews)
"Nice place. Good location."
United States
Rob M.
$389 nightly
The price is $424
Sep 3 - Sep 4
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (88 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
$369 nightly
The price is $402
Sep 2 - Sep 3
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (59 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.
$345 nightly
The price is $376
Sep 7 - Sep 8
Total with taxes and fees
Historic Home in the West End. Private Parking.

19. Stylish Brownstone Downtown Free St|Perfect Getaway for 2

Stylish Brownstone Downtown Free St|Perfect Getaway for 2
Downtown Portland
10.0 out of 10, Exceptional, (44 reviews)
"What a great stay! The rental property was absolutely fantastic! Can't wait to come back! Highly recommend staying here. "
United States
Ken C.
$640 nightly
The price is $698
Aug 21 - Aug 22
Total with taxes and fees
Stylish Brownstone Downtown Free St|Perfect Getaway for 2

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, (164 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
$811 nightly
The price is $884
Aug 19 - Aug 20
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

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 $180 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?

Quintessential Maine Beach Cottage: Visitors like this South Portland vacation home rental. It is located on the beach and has a private yard, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

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 Bug Light and Maine Mall.

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.