Holiday Homes in South Portland

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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 €584
includes taxes & fees
12 Nov - 13 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 €311
includes taxes & fees
9 Nov - 10 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

3. 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 €546
includes taxes & fees
9 Nov - 10 Nov
Spacious Portland Home + Parking

4. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (10 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
The price is €355
includes taxes & fees
11 Nov - 12 Nov
Chic 3-bedroom house in Munjoy Hill with off-street parking.

5. Charming West End Victorian

Charming West End Victorian
Parkside
The price is €648
includes taxes & fees
1 Dec - 2 Dec
Charming West End Victorian

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 €484
includes taxes & fees
9 Nov - 10 Nov
The 87th Townhome by Everrow

7. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €311
includes taxes & fees
9 Nov - 10 Nov
Quiet Spot in lovely Freeport neighborhood

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 €412
includes taxes & fees
11 Nov - 12 Nov
Fully Updated Airy Historic Home in South Freeport

9. 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 €474
includes taxes & fees
9 Nov - 10 Nov
Modern & Sunny East End House.

10. • Quiet 3BR Home Close to Biddeford Beaches

• Quiet 3BR Home Close to Biddeford Beaches
Biddeford
6.0 out of 10, (1 review)
"This place was okay- it served our needs. A few complaints- generally a dingy smell throughout the house, felt damp. The bathroom shower curtain has no liner so the curtain itself was very moldy. The grass wasnt mowed so I worried about ticks. The water tasted a little musty too but maybe thats just a Maine thing? Also the communication was pretty terrible with both the vrbo host and the property management company and I had a lot of trouble contacting them and getting the receipts I needed....
United States
Ellen B.
The price is €464
includes taxes & fees
15 Nov - 16 Nov
• Quiet 3BR Home Close to Biddeford Beaches

11. 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 €566
includes taxes & fees
9 Nov - 10 Nov
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

12. 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 €385
includes taxes & fees
9 Nov - 10 Nov
Seaside Retreat by Everrow

13. 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 €318
includes taxes & fees
10 Nov - 11 Nov
Orchid Harbor, Bailey Island 3BR

14. 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 €779
includes taxes & fees
9 Nov - 10 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.

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 €315
includes taxes & fees
16 Nov - 17 Nov
Mere Point Sunrise Views at Eastern Shore!

16. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake
Standish
The price is €665
includes taxes & fees
9 Nov - 10 Nov
New and Spacious Family Home Close to Sebago Lake

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 €685
includes taxes & fees
22 Nov - 23 Nov
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

18. 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 €950
includes taxes & fees
10 Nov - 11 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

19. 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
7.6 out of 10, Good, (4 reviews)
"Overall all nice stay. Thank you"
United States
Hope T.
The price is €290
includes taxes & fees
9 Nov - 10 Nov
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

20. 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 €478
includes taxes & fees
13 Nov - 14 Nov
Townhome: 10 Min to Beach by Everrow
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.