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Our top choices for South Portland holiday homes

"Excellent in every way."

HK$2,095 total

includes taxes & fees

15 Sept - 16 Sept

HK$5,767 total

includes taxes & fees

22 Sept - 23 Sept

HK$4,543 total

includes taxes & fees

25 Aug - 26 Aug

"Lovely and quiet. Just what I had hoped for. "

"Check in was simple. Quaint place. "

HK$1,390 total

includes taxes & fees

25 Aug - 26 Aug

"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "

HK$3,595 total

includes taxes & fees

26 Aug - 27 Aug

"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "

HK$1,789 total

includes taxes & fees

26 Aug - 27 Aug

"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"

HK$1,390 total

includes taxes & fees

1 Sept - 2 Sept

"Great place for us to use as a base as we made our way through Maine!"

HK$1,389 total

includes taxes & fees

1 Sept - 2 Sept

"Good location near lots of hiking and not far from Portland "

HK$2,735 total

includes taxes & fees

1 Sept - 2 Sept

"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."

HK$2,833 total

includes taxes & fees

25 Aug - 26 Aug

"A clean, beautiful home. It had lots of amenities and space. We had every thing we needed. It felt like home. We will definitely stay there again. "

HK$4,006 total

includes taxes & fees

12 Sept - 13 Sept

"Charming cabin. Well maintained. Loved my stay! Highly recommend."

HK$1,468 total

includes taxes & fees

9 Sept - 10 Sept

"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "

HK$3,327 total

includes taxes & fees

2 Sept - 3 Sept

"The place really was amazing and I would certainly stay again. If I could point out just one pc of advice the floors needed mopping very badly. Thank you for sharing your place with us we made some very special and wonderful memories. "

HK$3,169 total

includes taxes & fees

11 Sept - 12 Sept

Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

HK$1,399 total

includes taxes & fees

10 Sept - 11 Sept

"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."

HK$3,693 total

includes taxes & fees

21 Sept - 22 Sept