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Holiday Homes in South Portland

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for South Portland holiday homes

Property grounds

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, just like pictures "
United States
Evan M.
The price is NZ$499
includes taxes & fees
17 June - 18 June
South Portland Beach area rental
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (10 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$950
includes taxes & fees
17 June - 18 June
Willard Square Family Home
Living area

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, (1 review)
"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.
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
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, (60 reviews)
"Nice place. Good location."
United States
Rob M.
The price is NZ$644
includes taxes & fees
29 June - 30 June
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Property grounds

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (10 reviews)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
Orchid Harbor, Bailey Island 3BR
Interior

3 Bedroom 2 bath spacious beach house - 2nd house in from the beach!

3 Bedroom 2 bath spacious beach house - 2nd house in from the beach!
Old Orchard Beach
The price is NZ$2,506
includes taxes & fees
8 July - 9 July
3 Bedroom 2 bath spacious beach house - 2nd house in from the beach!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$624
includes taxes & fees
22 June - 23 June
Full sized home
Exterior detail

30 Acres with Woodland Trails and Playground

30 Acres with Woodland Trails and Playground
Freeport
10.0 out of 10, Exceptional, (1 review)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
United States
Zoraida
30 Acres with Woodland Trails and Playground
Fridge, microwave, oven, stovetop

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."
United States
Jake P.
The price is NZ$1,660
includes taxes & fees
29 June - 30 June
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
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 NZ$853
includes taxes & fees
21 June - 22 June
Adorable Seaside Cottage
Property grounds

The Brunswick #450 by Bayley Vacation Rentals

The Brunswick #450 by Bayley Vacation Rentals
Old Orchard Beach
6.0 out of 10, (1 review)
"The view was what sold us on the property and it delivered. But being from out of the area, we had no idea that we were going to be staying above a noisy bar with live music going late into the evening that we could hear even with the windows closed. If you want a party scene, this is a great spot. But if you're looking for ocean-front relaxation, I'd go elsewhere.Also, just know that the bathroom leaves a bit to be desired. The shower curtain was moldy and the tub-to-shower switch didn't fully...
United States
Christie H.
The price is NZ$1,843
includes taxes & fees
30 June - 1 July
The Brunswick #450 by Bayley Vacation Rentals
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, (7 reviews)
"The house worked perfectly for our family. We had a great stay."
United States
Judy F.
The price is NZ$850
includes taxes & fees
17 June - 18 June
OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
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, (97 reviews)
"Cozy and clean great location "
United States
Michele F.
The price is NZ$1,177
includes taxes & fees
28 June - 29 June
The Globe House on Munjoy Hill - Walk to Breweries
Terrace/patio

Bougie Beach Bungalow

Bougie Beach Bungalow
Old Orchard Beach
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful, clean, close to all activities."
United States
Michelle N.
The price is NZ$729
includes taxes & fees
13 July - 14 July
Bougie Beach Bungalow
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 NZ$614
includes taxes & fees
23 June - 24 June
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Outdoor dining

Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.8 out of 10, Excellent, (3 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is NZ$1,444
includes taxes & fees
28 June - 29 June
Spacious Portland Home + Parking
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, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$1,060
includes taxes & fees
18 June - 19 June
Modern & Sunny House Steps from the Promenade. Private Parking!
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 NZ$1,132
includes taxes & fees
17 June - 18 June
Little Miss Cottages - 5 Seaview House
Smart TV

Walk to Beach | Patio | Full Kitchen | Parking

Walk to Beach | Patio | Full Kitchen | Parking
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"Very nice property, would stay again!"
United States
Jason N.
The price is NZ$934
includes taxes & fees
18 June - 19 June
Walk to Beach | Patio | Full Kitchen | Parking
Property grounds

Maine Oceanfront Retreat

Maine Oceanfront Retreat
Brunswick
9.4 out of 10, Exceptional, (3 reviews)
"Gorgeous views house is extremely well equipped "
United States
Cary C.
Maine Oceanfront 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

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

8/10 Good
"Room was overall clean but we did notice some mold on the shower curtains."
Sean 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Portland

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews
22,279
Accommodation
777 Holiday Homes
Lowest Price
NZ$131
Highest Price
NZ$733