South Portland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in South Portland

Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is ￥28,424
￥42,537 total
includes taxes & fees
Dec 7 - Dec 8
The Weldon Hotel
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

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

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Property grounds
Quintessential Maine Beach Cottage

Quintessential Maine Beach Cottage

Goose Rocks Beach
10.0 out of 10, Exceptional, (137)
"Incredible stay in Maine with our dog. Everything was perfect!!!!"
United States
David Y.
Quintessential Maine Beach Cottage
Terrace/patio
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
9.8 out of 10, Exceptional, (124)
"House was beautiful! Comfy beds, amazing views,great location!"
United States
Katherine C.
The Moonglow! A beautiful ocean view house in Biddeford!
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

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

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Exterior
Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape

Raymond
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
Smart TV
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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

Old Orchard Beach
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Outdoor dining
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"Made a great place for a business retreat. WiFi worked well and we had plenty of space to spread out."
United States
dan b.
The price is ￥92,282
￥191,603 total
includes taxes & fees
Nov 16 - Nov 17
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Fridge, microwave, oven, stovetop
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

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

Saco
10.0 out of 10, Exceptional, (104)
"Such a beautiful home in an amazing location! "
United States
Michelle H.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Beach nearby
2 min walk to the beach. Pet friendly condo

2 min walk to the beach. Pet friendly condo

Old Orchard Beach
8.2 out of 10, Very Good, (41)
"Over all it was good, bathroom was off bedroom, not convenient for other guest staying on futon in living room. Backyard for dogs was very small, but enough space for the pups to do their duty. In all it worked for the few days we were there!"
United States
Cindy H.
2 min walk to the beach. Pet friendly condo
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very Good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is ￥12,183
￥23,291 total
includes taxes & fees
Nov 16 - Nov 17
In-town no frills 2 bedroom apt
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"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!"
United States
Anonymous traveler
The price is ￥10,559
￥21,667 total
includes taxes & fees
Nov 14 - Nov 15
Studio Unit Walkable Everywhere
TV, DVD player, books
Charming cottage with outdoor space, full kitchen, & WiFi - near beach

Charming cottage with outdoor space, full kitchen, & WiFi - near beach

Goose Rocks Beach
9.4 out of 10, Exceptional, (34)
"Wonderful space for family fun"
United States
Rachel E.
Charming cottage with outdoor space, full kitchen, & WiFi - near beach
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (167)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Property grounds
Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Raymond
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."
United States
Brian C.
Private Lakefront Estate with 180 Degree Views
Beach
Little Miss Cottages - Two Bedroom Cottage

Little Miss Cottages - Two Bedroom Cottage

Old Orchard Beach
9.0 out of 10, Wonderful, (4)
"It was a very enjoyable weekend stay. Cottage was clean and comfortable. The water heater was a bit noisy as was the traffic noise at the front bedroom, but otherwise, could not have ask for more. Perfect access to beach. "
United States
Lynne M.
The price is ￥20,798
￥45,004 total
includes taxes & fees
Dec 2 - Dec 3
Little Miss Cottages - Two Bedroom Cottage
On the beach, sun loungers
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Old Orchard Beach
9.8 out of 10, Exceptional, (44)
"Great house with lots of room for a big family. So close to the beach with great views. Great outdoor spaces as well! "
United States
Moria B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

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

Old Orchard Beach
9.8 out of 10, Exceptional, (224)
"The view off the deck was breathtaking "
United States
Raymond
The price is ￥26,961
￥52,561 total
includes taxes & fees
Nov 21 - Nov 22
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
2 bedrooms, WiFi, bed sheets
The Dollhouse

The Dollhouse

Old Orchard Beach
9.2 out of 10, Wonderful, (5)
"We had a great time! The place was exactly like the pictures. It was clean and had lots of amenities. My only suggestion would have more towels because we had five people and four bath towels. "
United States
Molly D.
The price is ￥69,620
￥115,683 total
includes taxes & fees
Nov 14 - Nov 15
The Dollhouse
Fridge, microwave, oven, stovetop
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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

Old Orchard Beach
9.8 out of 10, Exceptional, (64)
"My wife and I both enjoyed our stay and found the unit to be very cute, clean and comfortable. The owners were also quite nice and communicated very well whenever we reached out to them. We had a great stay!"
United States
Russell R.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The 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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Top South Portland Hotel Reviews

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Absolutely "
Philip 1-night trip
Posted 22 hours ago
Tru by Hilton Portland Airport Area

Find out more about South Portland

Search for holiday rentals in South Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in South Portland using one of the methods below:

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Look no further and take a look at our great range of rental properties in 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?

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 Maine Mall and Bug Light.

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.