Holiday Homes in South Portland

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for South Portland holiday homes

Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is €458
includes taxes & fees
9 May - 10 May
Modern Getaway by the Sea
Beach nearby

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
The price is €248
includes taxes & fees
10 May - 11 May
South Portland Beach area rental
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home
Interior

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (59 reviews)
"Nice place. Good location."
United States
Rob M.
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Beach nearby, sun-loungers, beach towels

Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean
Old Orchard Beach
10.0 out of 10, Exceptional, (58 reviews)
"Had a great winter stay. House was super clean, well equipped, and had comfortable furniture. The location was perfect. A great ocean view from living room and then simply crossing the street for a walk on the beach. "
United States
Erin S.
The price is €417
includes taxes & fees
3 May - 4 May
Beach House ∆ Prime Location ∆ Steps to the Ocean
Living area

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Old Orchard Beach
9.4 out of 10, Exceptional, (15 reviews)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is €472
includes taxes & fees
7 May - 8 May
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is €338
includes taxes & fees
14 May - 15 May
Full sized home
Outdoor dining

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

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (40 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is €404
includes taxes & fees
7 May - 8 May
Modern & Sunny House Steps from the Promenade. Private Parking!
Exterior

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.2 out of 10, Wonderful, (5 reviews)
"Great location"
United States
Mark J.
The price is €354
includes taxes & fees
4 May - 5 May
The 87th Townhome - Local Landmark
Outdoor dining

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The Globe House on Munjoy Hill - Walk to Breweries
Beach

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
The price is €234
includes taxes & fees
15 May - 16 May
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Exterior

OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA

OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
Old Orchard Beach
10.0 out of 10, Exceptional, (6 reviews)
"The house worked perfectly for our family. We had a great stay."
United States
Judy F.
The price is €419
includes taxes & fees
4 May - 5 May
OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
Interior

Adorable Seaside Cottage

Adorable Seaside Cottage
Old Orchard Beach
8.0 out of 10, Very good, (2 reviews)
"Overall nice small place, owner responded quickly to issues. "
United States
Qi L.
The price is €331
includes taxes & fees
4 May - 5 May
Adorable Seaside Cottage
Outdoor dining

Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub

Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub
Old Orchard Beach
9.0 out of 10, Wonderful, (25 reviews)
"We loved our stay at the Bliss Beach House! The sky deck provided a huge area to relax, enjoy the view and even had a hot tub. The kitchen was spacious with plenty of seating and had everything we needed for our stay. Jason was great with communication before and during our stay. "
United States
Laurie O.
The price is €516
includes taxes & fees
3 May - 4 May
Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub
1 bedroom, Internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is €241
includes taxes & fees
10 May - 11 May
Charming 1-bedroom ADU in wonderful Portland neighborhood
Smart TV, fireplace, books

The Sea Gaze - 5BR with Beach Path

The Sea Gaze - 5BR with Beach Path
Old Orchard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and great location "
United States
Nicole K.
The price is €467
includes taxes & fees
3 May - 4 May
The Sea Gaze - 5BR with Beach Path
Smart TV

Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
8.0 out of 10, Very good, (1 review)
"The only big issue was that the VRBO listing gave us the wrong address. It sent us to Scarborough instead of Saco. Luckily we were familiar with the area and I knew that Saco was close to Old Orchard Beach, which was mentioned in the listing, so I did a google map search of the same address in Saco and it looked like the pictures. My elderly parents were relieved that we didn’t get scammed. Lol. The place was clean and large and easy to get on the highway. It’s 2 and a half baths, not 3 full...
United States
Stacy H.
The price is €451
includes taxes & fees
3 May - 4 May
Huge New Townhome 10mins from the Beach
Interior

Spacious 5BR Family Dream with Private Beach Access

Spacious 5BR Family Dream with Private Beach Access
Old Orchard Beach
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.
Spacious 5BR Family Dream with Private Beach Access
Property grounds

Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Great property"
United States
Scott D.
The price is €1,484
includes taxes & fees
4 May - 5 May
Classic New England Waterfront House Big Lawn Beautiful Sunrise
Interior

Little Miss Cottages - 5 Seaview House

Little Miss Cottages - 5 Seaview House
Old Orchard Beach
6.0 out of 10, (1 review)
"Low amenities, kitchenware. "
United States
Sopheakrith
The price is €564
includes taxes & fees
18 May - 19 May
Little Miss Cottages - 5 Seaview House
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

Courtyard by Marriott Portland Airport

Courtyard by Marriott Portland Airport

10/10 Excellent
"Property was close to the mall and major roads which was very convenient. Only 15 minutes into downtown for an event and they were very accommodating to a late check out request."
Geoffrey 1-night trip
Posted 18 hours ago
Courtyard by Marriott Portland Airport

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews
359
Accommodation
760 Holiday Homes
Lowest Price
€234
Highest Price
€1,484