South Portland Holiday Rentals

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Check prices for these dates

Tonight
17 Jul - 18 Jul
Tomorrow
18 Jul - 19 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in South Portland

The Weldon Hotel
Relax in a spacious living area with a sofa, dining table, and flat-screen TV.

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (65)
"Absolutely beautiful place to stay. "
The price is HK$2,732
HK$3,567 total
includes taxes & fees
23 Jul - 24 Jul
The Weldon Hotel
68 East Grand Ave
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a marble countertop, and a sink.

68 East Grand Ave

3.0 star property
8.0 out of 10, Very good, (4)
"nice place close to all"
68 East Grand Ave
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

The price is HK$1,030
HK$1,611 total
includes taxes & fees
22 Jul - 23 Jul
Studio Unit Walkable Everywhere
Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.
Relax in a comfortable bedroom with a plush sofa, decorative headboard, and a cozy rug.

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

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 Beautiful Home One Bedroom Private Bathroom in Portland Maine.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Kitchen area with microwave, toaster, refrigerator, and sink.

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

9.8 out of 10, Exceptional, (48)
"Very nice property to stay at in Old Orchard Beach! It’s a very quiet neighborhood with a fully enclosed backyard, which was nice for my dog. It’s only a 15 minute walk to the beach, which is very convenient as well. Only thing that I would have liked was to have access to regular cable on the tv, since I couldn’t watch NESN with Roku. But still would give this place 5 stars! We had a lovely time. 😊"
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Gorgeous ocean-front home with stunning beach views
Guests can enjoy a leisurely day on the beach with access to sun loungers and umbrellas.

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (114)
"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
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (2)
"It was a privilege to have the opportunity to experience this truly amazing property. First of all, the tiny house was immaculate, and every available space was utilized perfectly. The outdoor space was so comfortable, I spent every morning on the deck reading, and we spent every evening around the fire pit. The boys explored the woods around the creek and I cooked three meals a day in that tiny kitchen! It’s hard to believe that four of us were so comfortable, but it is a testament to the hosts...
The price is HK$1,943
HK$2,426 total
includes taxes & fees
30 Jul - 31 Jul
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
100 feet from the ocean 3 bedroom cottage 420 friendly
Walk along the boardwalk to the beach, flanked by rope barriers and a welcoming sign.

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly
2 bedroom cottage
Cozy living space with a kitchenette, sofa, dining table, and bench.

2 bedroom cottage

9.6 out of 10, Exceptional, (4)
"quiet, clean, short walk to beach"
2 bedroom cottage
Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach
Beach

Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

8.0 out of 10, Very good, (3)
"Loved how close it was to everything,could be a little more updated on a couple of things"
Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Relax in a serene beachside setting with an outdoor seating area featuring a round table and comfortable chairs.

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (61)
"Beautiful location even in the offseason, gorgeous house with plenty of room for guests. Very close to Portland for a nice dinner and some drinks. We also went and played some golf at summit in OOB and had a blast. Outdoor grill was perfect and overall we had a great time! Excellent host excellent location and perfect for what we needed. Would recommend highly."
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Little Miss Cottages
Relax in a serene outdoor space with Adirondack chairs, a picnic table, and a fire pit.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (83)
"Place was great "
Little Miss Cottages
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Enjoy a game of volleyball on this expansive beach with a clear view of the ocean.

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."
The price is HK$3,132
HK$4,843 total
includes taxes & fees
29 Jul - 30 Jul
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Smart TV

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

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Enjoy the ocean view from this spacious balcony with a table and two chairs.

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

10.0 out of 10, Exceptional, (12)
"Stunning property and great location! "
The price is HK$4,203
HK$6,781 total
includes taxes & fees
20 Jul - 21 Jul
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Beach across the Street. Pets OK
Kitchen area with a modern gas stove, stainless steel sink, and coffee maker.

Beach across the Street. Pets OK

8.8 out of 10, Excellent, (27)
"Perfect spot! Right near the beach and walking distance to all the best places. Very clean and chill little place perfect for what I was going for."
The price is HK$1,531
HK$2,618 total
includes taxes & fees
24 Jul - 25 Jul
Beach across the Street. Pets OK
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Relax on the deck with a view of the calm lake, featuring comfortable seating and a barbecue grill.

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Beachfront Unit 17 | Right on Old Orchard Beach!
Enjoy ocean views from this patio, featuring a barbecue grill and comfortable seating.

Beachfront Unit 17 | Right on Old Orchard Beach!

10.0 out of 10, Exceptional, (1)
"It was Amazing right next to the beach , def will be coming back !!"
Beachfront Unit 17 | Right on Old Orchard Beach!
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Enjoy a tranquil beach experience with a volleyball net set up for recreational activities.

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

8.6 out of 10, Excellent, (55)
"Easy access and check in. The location was just what we wanted with it close to the beach."
The price is HK$3,524
HK$5,330 total
includes taxes & fees
3 Aug - 4 Aug
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Luxury apartment near Old Orchard Beach
Compact kitchen with microwave, stainless steel sink, and black refrigerator, featuring a minimalist aesthetic with dark cabinetry and a white countertop.

Luxury apartment near Old Orchard Beach

10.0 out of 10, Exceptional, (1)
"Very nice apartment, very clean."
The price is HK$1,554
HK$1,942 total
includes taxes & fees
20 Jul - 21 Jul
Luxury apartment near Old Orchard Beach
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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Frequently asked questions

Can I find holiday rentals in South Portland?

Yes, there are holiday rentals close to the most popular sights in South Portland, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that South Portland has to offer?

Charming 3 bedroom lake house on Damariscotta Lake.: This holiday home rental outside of South Portland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in South Portland?

With 56 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in South Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Portland. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.