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

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for South Portland vacation homes

Exterior

1. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 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 ￥47,817
￥96,334 total
includes taxes & fees
Aug 23 - Aug 24
Willard Square Family Home
Interior

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."
United States
Rob M.
The price is ￥23,263
￥68,791 total
includes taxes & fees
Sep 3 - Sep 4
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior

3. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is ￥29,487
￥66,367 total
includes taxes & fees
Sep 8 - Sep 9
Tranquility between the Lakes & Sea
Outdoor dining

4. 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)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is ￥57,062
￥92,949 total
includes taxes & fees
Sep 9 - Sep 10
Modern & Sunny House Steps from the Promenade. Private Parking!
Beach nearby

5. Beachwood Cottage by Bayley Vacation Rentals

Beachwood Cottage by Bayley Vacation Rentals
Grand Beach
9.8 out of 10, Exceptional, (15 reviews)
"Great place Location was excellent and there are many activities nearby. The beach was just across the street! "
United States
Douglas K.
Beachwood Cottage by Bayley Vacation Rentals
Outdoor dining

6. 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 ￥48,215
￥129,520 total
includes taxes & fees
Aug 30 - Aug 31
Spacious Portland Home + Parking
Interior

7. Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage

Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
Cape Elizabeth
10.0 out of 10, Exceptional, (6 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is ￥71,726
￥138,989 total
includes taxes & fees
Aug 24 - Aug 25
Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
TV, fireplace

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

Rare West End Home • Walk to Old Port, Harbor View
West End
10.0 out of 10, Exceptional, (12 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is ￥76,067
￥134,538 total
includes taxes & fees
Aug 27 - Aug 28
Rare West End Home • Walk to Old Port, Harbor View
Exterior

9. 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 ￥51,841
￥114,216 total
includes taxes & fees
Sep 13 - Sep 14
The 87th Townhome - Local Landmark
Interior

10. Adorable Seaside Cottage

Adorable Seaside Cottage
Old Orchard Beach
8.6 out of 10, Excellent, (4 reviews)
"Overall nice small place, owner responded quickly to issues. "
United States
Qi L.
The price is ￥25,133
￥80,905 total
includes taxes & fees
Sep 8 - Sep 9
Adorable Seaside Cottage
Dining

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is ￥79,217
￥175,820 total
includes taxes & fees
Aug 24 - Aug 25
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Interior

12. Niblet Cottage by Bayley Vacation Rentals

Niblet Cottage by Bayley Vacation Rentals
Grand Beach
8.0 out of 10, Very Good, (14 reviews)
"Absolutely wonderful two bedroom pet friendly house. Close to Old Orchard Pier. Bayleys Realtor accessible at anytime if needed. Would definitely return!"
United States
Denise B.
The price is ￥48,741
￥202,224 total
includes taxes & fees
Aug 22 - Aug 23
Niblet Cottage by Bayley Vacation Rentals
Interior

13. 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, (17 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is ￥101,053
￥170,434 total
includes taxes & fees
Sep 9 - Sep 10
Spacious 4-bedroom house located in the heart of Portland, ME.
Smart TV

14. Walk to Beach | Patio | Full Kitchen | Parking

Walk to Beach | Patio | Full Kitchen | Parking
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"Very nice property, would stay again!"
United States
Jason N.
The price is ￥27,574
￥85,825 total
includes taxes & fees
Sep 7 - Sep 8
Walk to Beach | Patio | Full Kitchen | Parking
Coffee/tea maker, fridge, microwave, oven

15. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space
Downtown Portland
The price is ￥137,713
￥254,869 total
includes taxes & fees
Aug 18 - Aug 19
Steps to Old Port, balcony, private outdoor space
Interior

16. 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.
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
TV, offices

17. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is ￥36,022
￥122,309 total
includes taxes & fees
Aug 19 - Aug 20
Windham Lakefront: Fire Pit and Modern Comforts
Beach

18. 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
6.0 out of 10, (1 review)
"Overall, value property. It's a very old home that was slightly renovated. Pros. 3 bedrooms, washer dryer, good price Cons. Smelled musty, pans not usable for cooking, small living room.Host was great with communication, and the stay was worth the price."
United States
Renee D.
The price is ￥19,924
￥54,727 total
includes taxes & fees
Sep 11 - Sep 12
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
TV, offices

19. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
Fully Updated Airy Historic Home in South Freeport
Microwave, oven, stovetop, dishwasher

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, (12 reviews)
"Great place! Perfectly clean, would recommend!"
United States
Debbie F.
The price is ￥79,301
￥154,403 total
includes taxes & fees
Aug 19 - Aug 20
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"The Fireside Inn was an enjoyable stay for my family. We loved the heated outdoor pool. Parking was very convenient. The location was central to many areas. Staff were friendly and helpful. We would stay here again."
Eileen 3-night trip
Posted 3 hours ago
Fireside Inn & Suites Portland

Find out more about South Portland

South Portland Vacation Homes information

Number of reviews
217
Accommodation
777 Vacation Homes
Lowest Price
￥54,727
Highest Price
￥254,869