Holiday Homes in South Portland

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 June - 14 June
In four months
10 July - 12 July

Our top choices for South Portland holiday homes

Interior

Holiday Home in South Portland

Modern Getaway by the Sea
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is AU$719
includes taxes & fees
22 Mar - 23 Mar
Modern Getaway by the Sea
Exterior

Holiday Home in Willard Beach

Willard Square Family Home
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AU$740
includes taxes & fees
18 Mar - 19 Mar
Willard Square Family Home
Microwave, oven, stovetop, dishwasher

Holiday Home in South Portland

Toast to 2026! Free Champagne for all Jan / Feb Bookings
10.0 out of 10, Exceptional, (4 reviews)
"The house was very nice and had great accommodations for our group. The kitchen and living room was very accommodating for meals and hangouts and we were close to all of the activities we were looking to do"
United States
Justin R.
The price is AU$862
includes taxes & fees
5 Apr - 6 Apr
Toast to 2026! Free Champagne for all Jan / Feb Bookings
Interior

Holiday Home in West End

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.4 out of 10, Very good, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is AU$365
includes taxes & fees
18 Mar - 19 Mar
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Beach nearby, sun-loungers, beach towels

Holiday Home in Old Orchard Beach

Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (57 reviews)
"House was very nice, plenty of room, and accommodating."
United States
Joey S.
The price is AU$670
includes taxes & fees
18 Mar - 19 Mar
Beach House ∆ Prime Location ∆ Steps to the Ocean
Terrace/patio

Holiday Home in Harpswell

Full sized home
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is AU$518
includes taxes & fees
18 Mar - 19 Mar
Full sized home
Outdoor dining

Holiday Home in Munjoy Hill

Modern & Sunny House Steps from the Promenade. Private Parking!
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$472
includes taxes & fees
19 Mar - 20 Mar
Modern & Sunny House Steps from the Promenade. Private Parking!
Exterior

Holiday Home in West End

The 87th Townhome - Local Landmark
9.0 out of 10, Wonderful, (4 reviews)
"Great location"
United States
Mark J.
The price is AU$502
includes taxes & fees
18 Mar - 19 Mar
The 87th Townhome - Local Landmark
Living area

Holiday Home in Old Orchard Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
9.4 out of 10, Exceptional, (15 reviews)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is AU$734
includes taxes & fees
30 Mar - 31 Mar
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
3 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Old Orchard Beach

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful stay at Garett and Sophia’s beautiful Maine home! From booking to check in and check out Garett was extremely helpful with any questions. The property was just as described and perfect for our family of 3! Would highly recommend!"
United States
Taylor D.
The price is AU$500
includes taxes & fees
22 Mar - 23 Mar
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Smart TV

Holiday Home in Old Orchard Beach

The Dollhouse
9.2 out of 10, Wonderful, (5 reviews)
"Wonderful stay for a small bachelorette party! Right squeeze with 7 girls but great to have the place already decorated. Very close to the pier and lots of stores, restaurants, and places to go around. Host was very friendly and accommodating, answered questions and was flexible with any of our needs!"
United States
Margaret D.
The price is AU$1,022
includes taxes & fees
18 Mar - 19 Mar
The Dollhouse
Property grounds

Holiday Home in Cape Elizabeth

Modern Cottage with Peeks of Ocean Views
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is AU$611
includes taxes & fees
18 Mar - 19 Mar
Modern Cottage with Peeks of Ocean Views
Dining

Holiday Home in Old Orchard Beach

Seaglass Cottage by Bayley Vacation Rentals
The price is AU$1,683
includes taxes & fees
5 Apr - 6 Apr
Seaglass Cottage by Bayley Vacation Rentals
Interior

Holiday Home in Old Orchard Beach

Spacious 5BR Family Dream with Private Beach Access
9.0 out of 10, Wonderful, (4 reviews)
"Had a great stay. Plenty of amenities that made it nice since it's the winter months. "
United States
Bradford P.
The price is AU$749
includes taxes & fees
18 Mar - 19 Mar
Spacious 5BR Family Dream with Private Beach Access
Room

Holiday Home in Buxton

Victorian Farmhouse | Walk to Saco River
The price is AU$515
includes taxes & fees
31 Mar - 1 Apr
Victorian Farmhouse | Walk to Saco River
1 bedroom, Internet, bed sheets

Holiday Home in Back Cove

Charming 1-bedroom ADU in wonderful Portland neighborhood
The price is AU$394
includes taxes & fees
18 Mar - 19 Mar
Charming 1-bedroom ADU in wonderful Portland neighborhood
Beach towels

Holiday Home in Biddeford

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
9.8 out of 10, Exceptional, (10 reviews)
"We have stayed three times and will be back"
United States
Michael W.
Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
Beach nearby

Holiday Home in Old Orchard Beach

Charming Victorian beach house 5 bedrooms. 50 steps to the beach
9.6 out of 10, Exceptional, (18 reviews)
"We had a great time and it’s an awesome place. Can’t wait to rebook for next year. "
United States
Robert D.
The price is AU$1,200
includes taxes & fees
29 Mar - 30 Mar
Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Smart TV, fireplace, books

Holiday Home in Old Orchard Beach

The Sea Gaze - 5BR with Beach Path
10.0 out of 10, Exceptional, (1 review)
"Beautiful house and great location "
United States
Nicole K.
The price is AU$767
includes taxes & fees
22 Mar - 23 Mar
The Sea Gaze - 5BR with Beach Path
Exterior

Holiday Home in Biddeford

A historic treasure in Southern Maine, very unique and spacious
10.0 out of 10, Exceptional, (44 reviews)
"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "
United States
Jeanne C.
The price is AU$1,401
includes taxes & fees
22 Mar - 23 Mar
A historic treasure in Southern Maine, very unique and spacious
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

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent
"We had an awesome stay! This hotel is so clean and staff is so helpful and welcoming! Pool area was also nice. Breakfast was extended continental with yogurt and bagel bar. Coffee and tea available 24/7. Probably the nicest hotel by the mall. Two star rating with a 3-4 star vibe and all the hospitality you expect from a Hilton. Allysa is wonderful! Our room was immaculate…. Shout out to housekeeping as well! Can’t wait to see you all again. Great food choices in area as well!"
Melynda 1-night trip
Posted 3 hours ago
Spark by Hilton Portland Airport Maine Mall

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews
304
Accommodation
732 Holiday Homes
Lowest Price
AU$365
Highest Price
AU$1,683