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

South Portland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for South Portland vacation rentals

TV

1. The Coastal Connection

The Coastal Connection
Thorton Heights
7.2 out of 10, Good, (7 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is AED 424
AED 1,199 total
includes taxes & fees
21 Sep - 22 Sep
The Coastal Connection
Interior

2. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is AED 724
AED 1,185 total
includes taxes & fees
22 Sep - 23 Sep
Sunny Spot with Private Parking.
Interior

3. 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 AED 667
AED 1,355 total
includes taxes & fees
29 Sep - 30 Sep
Willard Beach–Apartment Near Portland & Parks
Beach nearby

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 AED 742
AED 1,701 total
includes taxes & fees
21 Sep - 22 Sep
Arlie`s Digs! - One Block To Willard Beach!
Smart TV, books

5. 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, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AED 771
AED 1,289 total
includes taxes & fees
21 Sep - 22 Sep
Peaceful & minutes from the Old Port with private parking
Exterior

6. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 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 AED 1,102
AED 2,220 total
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
Living area

7. 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.
The price is AED 1,752
AED 3,555 total
includes taxes & fees
24 Sep - 25 Sep
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
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.
The price is AED 603
AED 1,274 total
includes taxes & fees
19 Oct - 20 Oct
Willard Beach: Cozy Apartment with a King Size Bed
1 bedroom, WiFi, bed sheets

9. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (19 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is AED 328
AED 592 total
includes taxes & fees
6 Oct - 7 Oct
Studio Apartment near downtown Walkable!
TV

10. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.4 out of 10, Very good, (12 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 AED 309
AED 389 total
includes taxes & fees
28 Sep - 29 Sep
Portland 1-bedroom with enclosed porch & parking
Smart TV

11. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AED 481
AED 824 total
includes taxes & fees
21 Sep - 22 Sep
Beautiful 1st Floor Apartment & Amazing Shower
Interior

12. 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 and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AED 417
AED 1,415 total
includes taxes & fees
19 Oct - 20 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Property grounds

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

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is AED 513
AED 1,716 total
includes taxes & fees
21 Sep - 22 Sep
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Fitness facility

14. 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, (16 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
The price is AED 528
AED 655 total
includes taxes & fees
23 Sep - 24 Sep
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
Flat-screen TV, Netflix, books, streaming services

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (91 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is AED 545
AED 1,575 total
includes taxes & fees
22 Sep - 23 Sep
Walk to Old Port ♦ West End Condo ♦ Parking
Interior

16. 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, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is AED 489
AED 845 total
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
Property grounds

17. 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.
The price is AED 411
AED 1,093 total
includes taxes & fees
22 Sep - 23 Sep
Serenity between the lakes and seashore
Dining

18. Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (55 reviews)
"Great stay. The apartment is cute, clean, and in a perfect location. Parking was easy, and the mattress was very comfortable. Would definitely stay here again."
United States
Victoria M.
The price is AED 907
AED 1,385 total
includes taxes & fees
29 Sep - 30 Sep
Charming West End Hideaway. Private Parking
Interior

19. Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.2 out of 10, Wonderful, (37 reviews)
"Good location; great space."
United States
Marie O.
The price is AED 750
AED 1,574 total
includes taxes & fees
29 Sep - 30 Sep
Skyline 138: Charming West End Mansard Penthouse
Exterior detail

20. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (147 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AED 650
AED 1,017 total
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Portland Hotel Reviews

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

8/10 Good
"Room was very clean and well maintained. The only negative was that the body wash dispenser was empty in bathroom, which I let them know upon checkout. Breakfast was one of the best we’ve had in a hotel. We have stayed here twice and will definitely stay again. It is very close to the airport and shopping as well."
Carol 1-night trip
Posted 1 hour ago
Tru by Hilton Portland Airport Area

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 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.