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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for South Portland vacation rentals

Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (27 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
The price is AED 944
AED 1,473 total
includes taxes & fees
7 Jul - 8 Jul
Sunny Spot with Private Parking.
Outdoor dining

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)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is AED 1,021
AED 1,617 total
includes taxes & fees
12 Jul - 13 Jul
Peaceful & minutes from the Old Port with private parking
TV

The Coastal Connection

The Coastal Connection
Thorton Heights
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The Coastal Connection
Smart TV, fireplace, books

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, (1 review)
"Lovely and quiet. Just what I had hoped for. "
United States
Heather R.
Willard Beach: Cozy Apartment with a King Size Bed
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (10 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home
Living area

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, (1 review)
"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.
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Interior

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.
Willard Beach–Apartment Near Portland & Parks
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

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
The price is AED 1,335
AED 1,455 total
includes taxes & fees
2 Jul - 3 Jul
Fortland Island Campground
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (7 reviews)
"Maine Oyster Company was a highlight of the trip! "
United Kingdom
Tyler P.
The price is AED 579
AED 874 total
includes taxes & fees
2 Jul - 3 Jul
Studio Apartment near downtown Walkable!
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is AED 1,051
AED 1,634 total
includes taxes & fees
5 Jul - 6 Jul
Modern, Luxurious Cabin in the Woods - 03
Beach nearby, sun loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveler
The price is AED 536
AED 1,352 total
includes taxes & fees
1 Jul - 2 Jul
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is AED 955
AED 1,554 total
includes taxes & fees
29 Jun - 30 Jun
Large, luxurious geodesic dome - 04
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is AED 529
AED 1,025 total
includes taxes & fees
28 Jun - 29 Jun
Pine Point Beach private, quaint, charming studio.
Fridge, microwave, oven, stovetop

4 min walk to the beach. 1BD. Pets Ok FREE parking

4 min walk to the beach. 1BD. Pets Ok FREE parking
Old Orchard Beach
8.6 out of 10, Excellent, (18 reviews)
"Nice little beachside apartment. Was clean, the futon could use replacing as well as some of the blinds but overall the stay was fine, and the host resolved our parking issue quickly. "
United States
Jennifer S.
The price is AED 382
AED 973 total
includes taxes & fees
30 Jun - 1 Jul
4 min walk to the beach. 1BD. Pets Ok FREE parking
Fitness facility

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

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
The price is AED 684
AED 853 total
includes taxes & fees
1 Jul - 2 Jul
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,363 total
includes taxes & fees
1 Jul - 2 Jul
Full sized home
Interior

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, (38 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
The price is AED 779
AED 1,343 total
includes taxes & fees
28 Jun - 29 Jun
East end. Walk to food, beer and downtown fun.
Smart TV

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AED 602
AED 988 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful 1st Floor Apartment & Amazing Shower
Beach nearby

Adorable 2 bedroom cabin only 50ft from Beach

Adorable 2 bedroom cabin only 50ft from Beach
Old Orchard Beach
9.6 out of 10, Exceptional, (4 reviews)
The price is AED 2,663
AED 3,775 total
includes taxes & fees
24 Jul - 25 Jul
Adorable 2 bedroom cabin only 50ft from Beach
Outdoor dining

THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (9 reviews)
The price is AED 533
AED 661 total
includes taxes & fees
28 Jun - 29 Jun
THE LILLIPAD.Off-grid A frame. Sebago lake region!
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

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Exprience was very nice Staff was very nice and co-operative"
Bharat 1-night trip
Posted 9 hours ago
Clarion Pointe South Portland

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?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private Bathroom “No Kitchen”: Visitors like this South Portland vacation home rental. It is located on the beach and offers a fireplace, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and an electric kettle.

How many vacation rentals are there in South Portland?

With 29 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.