Holiday Homes in South Portland

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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Featured Holiday Homes in South Portland

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, ping pong, books

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (75)
"Just as advertised. Fun and happy space. Incredibly well located. Would return in an instant."
The Globe House on Munjoy Hill - Walk to Breweries
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Private kitchen

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

2.0 star property
8.0 out of 10, Very good, (1)
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (212)
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness. "
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
The Moonglow! A beautiful ocean view house in Biddeford!
Terrace/patio

The Moonglow! A beautiful ocean view house in Biddeford!

9.8 out of 10, Exceptional, (101)
"located right on the beach, we stayed for February vacation which was not exactly a beach day but the view from the 2nd floor living room was perfect. Close to town and easy to get to. Would recommend. "
The Moonglow! A beautiful ocean view house in Biddeford!
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House
Serenity between the lakes and seashore
Exterior

Serenity between the lakes and seashore

9.8 out of 10, Exceptional, (17)
"Truly represented on VBRO. We were very pleased. Clean and well stocked. Easy to get around area. 5 Stars from us. "
Serenity between the lakes and seashore
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (27)
"The house was just as cute as pictured, and the communication with our host was great - Jennifer was so responsive and welcoming! Great location, too! We were able to walk to the venue (PHOME) for a great show, and overall had an awesome weekend with our friends - great spot for a small group of friends! Thanks for the hospitality!"
The price is AU$572
includes taxes & fees
9 Mar - 10 Mar
Modern & Sunny House Steps from the Promenade. Private Parking!
Maine Cottage
Property grounds

Maine Cottage

9.8 out of 10, Exceptional, (73)
"Second time staying at this property and will definitely stay again !!! "
Maine Cottage
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
East Grand Ave Fabulous Cottage
Beach

East Grand Ave Fabulous Cottage

9.2 out of 10, Wonderful, (131)
"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "
East Grand Ave Fabulous Cottage
Sun-Soaked Coastal Cottage w/ Deck + Walk to Beach
Exterior

Sun-Soaked Coastal Cottage w/ Deck + Walk to Beach

9.0 out of 10, Wonderful, (24)
"This trip was our first time at Old Orchard Beach. The location was incredible. Michael, our point of contact, was very responsive and helpful. The property, being steps from the beach, had all the amenities you could ask for. I recommend this property to anyone."
Sun-Soaked Coastal Cottage w/ Deck + Walk to Beach
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Interior

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay with our family (including our 3yo). The home was exactly as described/photos show, and the view is simply amazing. Everything worked as expected, and the kids toys were an added bonus. Great communication with the host, would happily stay here again!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
Fridge, microwave, oven, stovetop

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

9.6 out of 10, Exceptional, (74)
"Enjoyed our stay to visit our Maine family.It snowed on Christmas Eve - just for us!Turned our Vrbo home into a winter wonderland!"
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel cot

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (40)
"Great place.... Very clean and everything you will need to stay. It was three levels and it had supplies needed for the beach (Beach wagon, chairs, towel, sand toys...). We stayed off season so most of the houses were vacant. We would definately come back again. I did send two messages to the owner, but did not get a response. "
The price is AU$783
includes taxes & fees
17 Mar - 18 Mar
Beach House ∆ Prime Location ∆ Steps to the Ocean
Quintessential Maine Beach Cottage
Property grounds

Quintessential Maine Beach Cottage

10.0 out of 10, Exceptional, (106)
"Loved our stay on the edge of the marsh! The house is adorable and well equipped. An ice storm the day prior to our arrival made pretty much every walkway in Maine (and in the driveway and walkaway to the house) an ice skating rink, but we managed not to break any hips. So peaceful watching the ice flows and ducks traveling down the marsh creek. The shells on Goose Rock Beach were plentiful and the seals that watched (laughed at?) us from afar as we prepped for a polar plunge (we chickened out...
Quintessential Maine Beach Cottage
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
On the beach, sun-loungers, beach towels

The Perfect Beach Escape: Cozy 4-Bedroom Retreat

10.0 out of 10, Exceptional, (95)
"We traveled to Old Orchard during February break. While OOB didn’t have a lot going on we were able to travel around Maine with an oceanfront home base. The beach was nearly empty for daily walks, plenty of sunshine to bundle up and sit on the upper deck in, and a lot of snow! We did enjoy a nor’easter while we were there. The driveway was cleared the next day and the front stairs were cleaned. We did have to do the deck out back to enjoy it. The house has everything you could need for a rental....
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
The Boathouse Cottage is a beachfront family retreat
Terrace/patio

The Boathouse Cottage is a beachfront family retreat

9.8 out of 10, Exceptional, (70)
"We were so pleased with how clean everything was, so very family friendly and so comfortable. Everything was great!"
The Boathouse Cottage is a beachfront family retreat
Elegant Orchard Retreat: Generous Yard & Patio
Beach

Elegant Orchard Retreat: Generous Yard & Patio

2.0 star property
10.0 out of 10, Exceptional, (4)
"It was a great spot to enjoy some quality time together and even though it was cold, we all enjoyed walking along the beach. Even our dog felt right at home"
Elegant Orchard Retreat: Generous Yard & Patio
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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Other property types in South Portland

Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (41)
"Very clean and comfortable! "
The price is AU$263
includes taxes & fees
23 Mar - 24 Mar
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views
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.