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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for South Portland holiday 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 NZ$990
includes taxes & fees
30 Aug - 31 Aug
Willard Square Family Home
Living area

2. 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, (2 reviews)
"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

3. 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.
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Outdoor dining

4. 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$1,182
includes taxes & fees
2 Aug - 3 Aug
Spacious Portland Home + Parking
Interior

5. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$697
includes taxes & fees
5 Aug - 6 Aug
Tranquility between the Lakes & Sea
TV, fireplace

6. 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 NZ$1,172
includes taxes & fees
4 Aug - 5 Aug
Rare West End Home • Walk to Old Port, Harbor View
Exterior

7. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.6 out of 10, Exceptional, (8 reviews)
"Great location"
United States
Mark J.
The price is NZ$1,264
includes taxes & fees
2 Aug - 3 Aug
The 87th Townhome - Local Landmark
Beach nearby

8. 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.
The price is NZ$2,110
includes taxes & fees
25 Aug - 26 Aug
Beachwood Cottage by Bayley Vacation Rentals
Interior

9. 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 NZ$859
includes taxes & fees
1 Sept - 2 Sept
Adorable Seaside Cottage
Terrace/patio

10. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (59 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$616
includes taxes & fees
12 Aug - 13 Aug
Full sized home
Interior

11. 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 NZ$1,799
includes taxes & fees
21 Aug - 22 Aug
Pastoral Tranquil Walkable to Trails Dining Shopping Secure Bike Boat Storage
Dining

12. Seaglass Cottage by Bayley Vacation Rentals

Seaglass Cottage by Bayley Vacation Rentals
Old Orchard Beach
8.0 out of 10, Very good, (1 review)
"Clean, convenient. Nice stay!"
United States
Kathryn G.
The price is NZ$2,188
includes taxes & fees
7 Aug - 8 Aug
Seaglass Cottage by Bayley Vacation Rentals
Dining

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is NZ$1,915
includes taxes & fees
9 Aug - 10 Aug
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Outdoor dining

14. 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$957
includes taxes & fees
1 Sept - 2 Sept
Modern & Sunny House Steps from the Promenade. Private Parking!
TV, offices

15. 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 NZ$1,379
includes taxes & fees
19 Aug - 20 Aug
Windham Lakefront: Fire Pit and Modern Comforts
Property grounds

16. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is NZ$992
includes taxes & fees
6 Aug - 7 Aug
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Interior

17. Niblet Cottage by Bayley Vacation Rentals

Niblet Cottage by Bayley Vacation Rentals
Grand Beach
8.0 out of 10, Very good, (13 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 NZ$2,283
includes taxes & fees
8 Aug - 9 Aug
Niblet Cottage by Bayley Vacation Rentals
Smart TV

18. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is NZ$1,636
includes taxes & fees
2 Aug - 3 Aug
Luxe 5 Bed/ 3 Bath with Game Room & AC
Smart TV

19. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
8.0 out of 10, Very good, (1 review)
"The only big issue was that the VRBO listing gave us the wrong address. It sent us to Scarborough instead of Saco. Luckily we were familiar with the area and I knew that Saco was close to Old Orchard Beach, which was mentioned in the listing, so I did a google map search of the same address in Saco and it looked like the pictures. My elderly parents were relieved that we didn’t get scammed. Lol. The place was clean and large and easy to get on the highway. It’s 2 and a half baths, not 3 full...
United States
Stacy H.
The price is NZ$973
includes taxes & fees
1 Sept - 2 Sept
Huge New Townhome 10mins from the Beach
Interior

20. 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, (15 reviews)
"Great place great location. "
United States
Chris f.
The price is NZ$1,961
includes taxes & fees
19 Aug - 20 Aug
Spacious 4-bedroom house located in the heart of Portland, ME.
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
"Nice hotel at an affordable price."
William 3-night trip
Posted 3 hours ago
Clarion Hotel Portland Airport ME

Find out more about South Portland

South Portland Holiday Homes information

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