Holiday Rentals in South Portland

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Holiday Rentals in South Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (82)
"Great spot, large space, cool design, clean, easy to walk all over town. "
The price is €237
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (64)
"The views from this house are amazing. It is literally steps away from the beach. We had a family gathering with all ages and everyone had a great time. The house is spacious, clean and comfortable. The owner was very responsive when we reached out. We were able to see fireworks from the balcony as we were there during the 4th. It is close enough to walk to the pier area for the arcade/rides and restaurants. We loved our time in this home and hope to return again!"
The price is €1,188
includes taxes & fees
2 Nov - 3 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

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

7.6 out of 10, Good, (4)
"Ease of beach access. "
Bright and airy condo with beachfront access and walkable entertainment nearby

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (50)
"We loved everything about our stay here. Perfect location right on Old Orchard Beach. The house is perfect for what we needed/wanted. Wish we could have stayed longer. We would definitely come back for a longer stay next time we’re in Maine. "
The price is €434
includes taxes & fees
13 Oct - 14 Oct
Beach House ∆ Prime Location ∆ Steps to the Ocean

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very smooth and easy check-in. Very nice room and bathroom. Thank you so much for letting us stay! "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

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

10.0 out of 10, Exceptional, (230)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

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

9.8 out of 10, Exceptional, (45)
"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 €386
includes taxes & fees
8 Nov - 9 Nov
350 Yards to the beach. Pet friendly!

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
9.0 out of 10, Wonderful, (14)
"Very responsive host, even got us a pack and play for our youngest! Perfect house for a beach stay! Would stay again! "
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

10.0 out of 10, Exceptional, (99)
"Would love to stay here again!! "
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Sebago Lake Cottage on Raymond Cape

10.0 out of 10, Exceptional, (48)
"Our family was up for a wedding so we came up to visit. This is a beautiful place. We will keep this in mind for the future. "
Sebago Lake Cottage on Raymond Cape

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

9.6 out of 10, Exceptional, (12)
"After a looong drive, it was a pleasure to land in our cozy tiny home cove. Carley’s cabin made a perfect home base—clean, comfortable, and thoughtfully stocked with everything we needed. The amenities were excellent, and it’s easy to forget you’re actually off the grid!Although we didn’t get a chance to use it, the outdoor patio is a beautifully put-together space and would be a great spot for gathering or relaxing.Carley was incredibly helpful when we ran into a few small issues and gave us...
The price is €272
includes taxes & fees
14 Oct - 15 Oct
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

Private Lakefront Estate with 180 Degree Views

10.0 out of 10, Exceptional, (7)
"This was a fabulous property in perfect location. The house and grounds were amazing. It was a sensational week."
Private Lakefront Estate with 180 Degree Views

2 min walk to the beach. Pet friendly condo

8.2 out of 10, Very good, (39)
"Host was very accommodating and easy to contact & communicate with. I'll definitely stay again! Highly recommended "
2 min walk to the beach. Pet friendly condo

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

9.8 out of 10, Exceptional, (64)
"Such a nice place for couples to stay. We really enjoyed our time. Highly recommend! "
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Direct Oceanfront/Beachfront Home in Saco, ME. Family Retreat sleeps 19 

9.8 out of 10, Exceptional, (39)
"Well equipped, very comfortable home with beautiful views. "
Direct Oceanfront/Beachfront Home in Saco, ME. Family Retreat sleeps 19 

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

9.8 out of 10, Exceptional, (9)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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

9.8 out of 10, Exceptional, (220)
"The Property had everything we needed to relax and have a great time."
The price is €301
includes taxes & fees
25 Oct - 26 Oct
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Portland holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Portland holiday rentals we have selected for you start as low as €237 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 holiday 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 holiday.

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 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?

Beach House ∆ Prime Location ∆ Steps to the Ocean: This holiday home rental outside of South Portland is located on the waterfront, and has a balcony, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in South Portland?

With 29 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 Bug Light and Maine Mall.

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.