A lighthouse, rocky coastline, and a sunset over the ocean.

Holiday Homes in South Portland

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for South Portland holiday homes

A building named Willard Square with a storefront and a red vehicle parked outside.

1. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is NZ$1,008
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A cozy living room with a sectional sofa, a white wood-burning stove, and large windows offering a view of the outdoors.

2. SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is NZ$1,800
includes taxes & fees
24 Sept - 25 Sept
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

3. 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, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is NZ$646
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A snow-covered landscape with a house and a tree.

4. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is NZ$530
includes taxes & fees
22 Sept - 23 Sept
Serenity between the lakes and seashore
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

5. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$958
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.
A two-story brick building with a front porch, a black door, and a window with a white frame.

6. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.4 out of 10, Exceptional, (9 reviews)
"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"
United States
Amy B.
The price is NZ$1,253
includes taxes & fees
20 Sept - 21 Sept
The 87th Townhome - Local Landmark
A window with a view of a snowy landscape and bare trees.

7. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$602
includes taxes & fees
13 Oct - 14 Oct
Tranquility between the Lakes & Sea
A two-story house with a balcony, a covered patio, and a fenced yard.

8. 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, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is NZ$1,118
includes taxes & fees
22 Sept - 23 Sept
The Globe House on Munjoy Hill - Walk to Breweries
A bedroom with a bed, a chair, a bookshelf, and a lamp.

9. ⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
Old Orchard Beach
10.0 out of 10, Exceptional, (9 reviews)
"This house was perfect."
United States
Courtney S.
The price is NZ$835
includes taxes & fees
20 Sept - 21 Sept
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

10. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Oakdale
10.0 out of 10, Exceptional, (1 review)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
United States
Andy W.
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

11. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is NZ$674
includes taxes & fees
17 Sept - 18 Sept
Quiet Spot in lovely Freeport desert pines neighborhood
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

12. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
An aerial view of a coastal residential area with beachfront properties, a main road, and a river.

13. Spacious 5BR Family Dream with Private Beach Access

Spacious 5BR Family Dream with Private Beach Access
Old Orchard Beach
8.6 out of 10, Excellent, (7 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 NZ$1,032
includes taxes & fees
17 Sept - 18 Sept
Spacious 5BR Family Dream with Private Beach Access
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

14. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is NZ$1,724
includes taxes & fees
22 Sept - 23 Sept
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A narrow hallway with white walls, a blue carpet, and a door leading outside.

15. Adorable Seaside Cottage

Adorable Seaside Cottage
Old Orchard Beach
8.0 out of 10, Very good, (5 reviews)
"Overall nice small place, owner responded quickly to issues. "
United States
Qi L.
The price is NZ$854
includes taxes & fees
14 Oct - 15 Oct
Adorable Seaside Cottage
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

16. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is NZ$2,244
includes taxes & fees
22 Sept - 23 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A rooftop deck with outdoor seating, a barbecue grill, and a view of the beach and ocean.

17. 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, (32 reviews)
"We had a wonderful time-the property was so close to the beach and within walking distance of the pier. The rooftop with all the seating and the hot tub was especially nice. And the owner was so easy to communicate with and very receptive to any questions we had."
United States
Michelle W.
The price is NZ$2,222
includes taxes & fees
12 Oct - 13 Oct
Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

18. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is NZ$864
includes taxes & fees
17 Sept - 18 Sept
Fully Updated Airy Historic Home in South Freeport
A living room with a grey sofa, two patterned armchairs, a round wicker coffee table, and a flat-screen TV mounted on the wall.

19. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
9.0 out of 10, Wonderful, (2 reviews)
"The location was very convenient. Easy drive to downtown Saco and Biddeford. As well as very quick access to the highway so Portland and other points are easy to get to. Ample parking."
United States
Ellen L.
The price is NZ$951
includes taxes & fees
17 Sept - 18 Sept
Huge New Townhome 10mins from the Beach
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a marble countertop.

20. The Links Lodge - Modern Golf and Beach Retreat

The Links Lodge - Modern Golf and Beach Retreat
Old Orchard Beach
10.0 out of 10, Exceptional, (13 reviews)
"Great place! Perfectly clean, would recommend!"
United States
Debbie F.
The price is NZ$1,214
includes taxes & fees
6 Oct - 7 Oct
The Links Lodge - Modern Golf and Beach Retreat
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

8/10 Good
"Furniture arrangements in rooms could have been better."
James 1-night trip
Posted 6 hours ago
Spark by Hilton Portland Airport Maine Mall

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews
Accommodation
779 Holiday Homes
Lowest Price
NZ$4,751
Highest Price
NZ$4,751