South Portland Vacation Rentals

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Vacation Rentals in South Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (76)
"Absolutely beautiful place to stay. "
The price is CA $578
CA $733 total
includes taxes & fees
Sep 8 - Sep 9
The Weldon Hotel

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (63)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
The price is CA $1,051
CA $1,994 total
includes taxes & fees
Sep 8 - Sep 9
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (217)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (75)
"Wonderful spot with great accommodations! Would definitely stay again!"
Grand Victorian on the Beach, Summer

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave

Bright and airy condo with beachfront access and walkable entertainment nearby

8.0 out of 10, Very good, (1)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (20)
"Stunning property and great location! "
The price is CA $405
CA $776 total
includes taxes & fees
Sep 3 - Sep 4
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (225)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.6 out of 10, Excellent, (12)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town

New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

10.0 out of 10, Exceptional, (4)
"Very clean and comfortable, we enjoyed our stay."
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (45)
"Great location. House was clean. "
The price is CA $258
CA $751 total
includes taxes & fees
Sep 15 - Sep 16
Beach House ∆ Prime Location ∆ Steps to the Ocean

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (36)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"Second time staying hear. Will continue to repeat"
Gorgeous ocean-front home with stunning beach views

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

9.8 out of 10, Exceptional, (43)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
The price is CA $378
CA $601 total
includes taxes & fees
Sep 4 - Sep 5
350 Yards to the beach. Pet friendly!

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (126)
"This unit surpassed our expectations. Excellent location, the unit was impeccable, had everything we needed and more.Highly recommend renting from Owner.. I know we will be!"
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

Luxury apartment near Old Orchard Beach

10.0 out of 10, Exceptional, (3)
"Very nice apartment, very clean."
The price is CA $272
CA $337 total
includes taxes & fees
Sep 3 - Sep 4
Luxury apartment near Old Orchard Beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (138)
"Great place. Perfect location if you want to be in the middle of it all."
The price is CA $378
CA $634 total
includes taxes & fees
Sep 15 - Sep 16
Oceanfront Condo! Spectacular Views From Private Large Balcony

Studio Unit Walkable Everywhere

8.0 out of 10, Very good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is CA $144
CA $243 total
includes taxes & fees
Sep 3 - Sep 4
Studio Unit Walkable Everywhere
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Portland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Portland vacation rentals we have selected for you start as low as CA $144 per night. Entering your travel dates in the search wizard 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. 

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 Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: Visitors like this South Portland vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in South Portland?

With 30 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.