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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is €530
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

2. 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 €343
includes taxes & fees
19 Oct - 20 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A window with a view of a snowy landscape and bare trees.

3. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is €285
includes taxes & fees
29 Sept - 30 Sept
Tranquility between the Lakes & Sea
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

4. Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.6 out of 10, Excellent, (4 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 €621
includes taxes & fees
27 Sept - 28 Sept
Spacious Portland Home + Parking
A living room with a sofa, a coffee table, and a vase on a windowsill.

5. Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View
West End
9.8 out of 10, Exceptional, (15 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is €588
includes taxes & fees
1 Oct - 2 Oct
Rare West End Home • Walk to Old Port, Harbor View
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 €620
includes taxes & fees
28 Sept - 29 Sept
The 87th Townhome - Local Landmark
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

7. 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 €492
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

8. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is €605
includes taxes & fees
1 Oct - 2 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A narrow hallway with white walls, a blue carpet, and a door leading outside.

9. 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 €409
includes taxes & fees
30 Sept - 1 Oct
Adorable Seaside Cottage
A living room with a grey sofa, two patterned armchairs, a round wicker coffee table, and a flat-screen TV mounted on the wall.

10. 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 €452
includes taxes & fees
27 Sept - 28 Sept
Huge New Townhome 10mins from the Beach
A picnic table by a lake with trees and a white fence in the background.

11. Couple's Glamping Getaway on Bonny Eagle Pond

Couple's Glamping Getaway on Bonny Eagle Pond
Buxton
10.0 out of 10, Exceptional, (14 reviews)
"Great location! Exceptionally clean and comfortable."
United States
ALYSSA
The price is €287
includes taxes & fees
6 Oct - 7 Oct
Couple's Glamping Getaway on Bonny Eagle Pond
A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

12. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €338
includes taxes & fees
25 Sept - 26 Sept
Quiet Spot in lovely Freeport neighborhood
A bedroom with a bed, a window with curtains, a wall-mounted lamp, and a view of the outside.

13. Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi

Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
Old Orchard Beach
The price is €391
includes taxes & fees
25 Sept - 26 Sept
Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
A cozy room with a wooden interior, featuring a white wicker sofa with blue and white patterned cushions, a matching armchair, and a small white table.

14. Little Miss Cottages - 5 Seaview House

Little Miss Cottages - 5 Seaview House
Old Orchard Beach
8.0 out of 10, Very good, (5 reviews)
"Low amenities, kitchenware. "
United States
Sopheakrith
Little Miss Cottages - 5 Seaview House
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

15. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (20 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is €878
includes taxes & fees
20 Oct - 21 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.

16. The Sea Gaze - 4BR with Beach Access

The Sea Gaze - 4BR with Beach Access
Old Orchard Beach
The Sea Gaze - 4BR with Beach Access
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a marble countertop.

17. 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 €587
includes taxes & fees
29 Sept - 30 Sept
The Links Lodge - Modern Golf and Beach Retreat
A two-story house with a blue exterior, white railings, and a brick chimney.

18. 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
9.6 out of 10, Exceptional, (11 reviews)
"Great location near beach. Space good for a big group with all necessary amenities."
United States
Rachel A.
The price is €469
includes taxes & fees
27 Sept - 28 Sept
OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
A bedroom with a bed, a chair, a bookshelf, and a lamp.

19. ⚓ 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)
The price is €417
includes taxes & fees
1 Oct - 2 Oct
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
A rooftop deck with outdoor seating, a barbecue grill, and a view of the beach and ocean.

20. 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 €642
includes taxes & fees
12 Oct - 13 Oct
Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Convenient location, great staff. No complimentary coffee in the lobby or breakfast area"
Susanne 1-night trip
Posted less than an hour ago
Clarion Hotel Portland Airport ME

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews
264
Accommodation
798 Holiday Homes
Lowest Price
€285
Highest Price
€878