South Portland Vacation Rentals

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Vacation Rentals in South Portland

Our top choices for South Portland vacation rentals

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (71)
"Absolutely beautiful place to stay. "
The price is CA $360
CA $497 total
includes taxes & fees
Sep 1 - Sep 2
The Weldon Hotel

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

9.8 out of 10, Exceptional, (215)
"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. "
The price is CA $468
CA $757 total
includes taxes & fees
Sep 1 - Sep 2
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
8.0 out of 10, Very good, (7)
"Great location. "
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

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 $1,872
CA $3,009 total
includes taxes & fees
Sep 5 - Sep 6
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

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

10.0 out of 10, Exceptional, (17)
"Stunning property and great location! "
The price is CA $548
CA $955 total
includes taxes & fees
Sep 15 - Sep 16
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views

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.

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

9.2 out of 10, Wonderful, (7)
The price is CA $343
CA $429 total
includes taxes & fees
Aug 26 - Aug 27
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

4-bedroom vacation home steps to Old Orchard Beach Pier

10.0 out of 10, Exceptional, (14)
"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"
4-bedroom vacation home steps to Old Orchard Beach Pier

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 $271
CA $475 total
includes taxes & fees
Aug 24 - Aug 25
350 Yards to the beach. Pet friendly!

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

7.4 out of 10, Good, (26)
"The cute apartment was clean with super comfy beds and very convenient to everything in OOB."
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

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

9.8 out of 10, Exceptional, (126)
"Right on the beach. Beautiful view. Clean and well appointed apartment Would definitely recommend and return "
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (54)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is CA $248
CA $413 total
includes taxes & fees
Sep 14 - Sep 15
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

2 min walk to the beach. Pet friendly condo

8.0 out of 10, Very good, (37)
"Host was very accommodating and easy to contact & communicate with. I'll definitely stay again! Highly recommended "
The price is CA $208
CA $398 total
includes taxes & fees
Sep 3 - Sep 4
2 min walk to the beach. Pet friendly condo

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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

10.0 out of 10, Exceptional, (2)
"A beautiful home, very clean, and a perfect location for us. Short walking distance to everything we wanted to do. "
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

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

9.8 out of 10, Exceptional, (42)
"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!
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

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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: You might want to consider this vacation home rental near South Portland, which offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in South Portland?

With 57 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.