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Check prices for these dates

Our top choices for South Portland holiday homes

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 £487
includes taxes & fees
18 Nov - 19 Nov
Willard Square Family Home

2. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is £253
includes taxes & fees
16 Nov - 17 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

3. Charming West End Victorian

Charming West End Victorian
Parkside
The price is £517
includes taxes & fees
1 Dec - 2 Dec
Charming West End Victorian

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 £439
includes taxes & fees
15 Nov - 16 Nov
Spacious Portland Home + Parking

5. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is £259
includes taxes & fees
14 Nov - 15 Nov
Quiet Spot in lovely Freeport neighborhood

6. The 87th Townhome by Everrow

The 87th Townhome by Everrow
West End
9.6 out of 10, Exceptional, (11 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 £388
includes taxes & fees
16 Nov - 17 Nov
The 87th Townhome by Everrow

7. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is £381
includes taxes & fees
16 Nov - 17 Nov
Modern & Sunny East End House.

8. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is £343
includes taxes & fees
14 Nov - 15 Nov
Fully Updated Airy Historic Home in South Freeport

9. • Quiet 3BR Home Close to Biddeford Beaches

• Quiet 3BR Home Close to Biddeford Beaches
Biddeford
8.0 out of 10, Very good, (2 reviews)
"Great spot for us to be for the week!"
United States
Brooke F.
The price is £376
includes taxes & fees
15 Nov - 16 Nov
• Quiet 3BR Home Close to Biddeford Beaches

10. Upscale OOB Beach House ♦ Seasonal Heated Pool

Upscale OOB Beach House ♦ Seasonal Heated Pool
Old Orchard Beach
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful remodel with plenty of beds and rooms. Came for son’s graduation from UNE. If we come back to OOB, would stay again in a heartbeat. "
United States
Kristen S.
The price is £361
includes taxes & fees
15 Nov - 16 Nov
Upscale OOB Beach House ♦ Seasonal Heated Pool

11. Seaside Retreat by Everrow

Seaside Retreat by Everrow
Old Orchard Beach
8.4 out of 10, Very good, (6 reviews)
"Overall nice small place, owner responded quickly to issues. "
United States
Qi L.
The price is £319
includes taxes & fees
15 Nov - 16 Nov
Seaside Retreat by Everrow

12. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is £306
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR

13. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is £494
includes taxes & fees
18 Nov - 19 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

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

Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"The property was very nice and what my family needed. It was exactly what I expected of a beach bungalow in the OOB area. The beds were surprising and so comfortable and while the shower was small, the water pressure was so nice. We would absolutely come back! The owner was very communicative and quick to respond."
United States
Amy S.
The price is £244
includes taxes & fees
15 Nov - 16 Nov
Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi

15. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is £256
includes taxes & fees
16 Nov - 17 Nov
Mere Point Sunrise Views at Eastern Shore!

16. Townhome: 10 Min to Beach by Everrow

Townhome: 10 Min to Beach by Everrow
Saco
9.4 out of 10, Exceptional, (3 reviews)
"The property is very close to I 95 making it very convenient to commute to portland. It is close to a grocery store. It was clean and the pictures were accurate. Our family of 6 had a nice stay."
United States
Krista B.
The price is £350
includes taxes & fees
13 Nov - 14 Nov
Townhome: 10 Min to Beach by Everrow

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is £571
includes taxes & fees
30 Nov - 1 Dec
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

18. 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, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is £649
includes taxes & fees
18 Nov - 19 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.

19. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
10.0 out of 10, Exceptional, (1 review)
"Nice, clean, good location.Would Recommend!"
United States
glen l.
The price is £334
includes taxes & fees
15 Nov - 16 Nov
Cozy Family Home w/ Beach Access

20. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is £760
includes taxes & fees
16 Nov - 17 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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.

Learn more about South Portland

Stroll along Willard Beach's sandy shores before exploring the charming Bug Light lighthouse park. Foodies can savour local flavours at welcoming restaurants, while shoppers browse the expansive Maine Mall for treasures.

A lighthouse on a rocky outcrop by the sea, with a metal railing and a cloudy sky.

Top reviews in South Portland