Holiday Homes in South Portland

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In one month

In two months

In three months

Featured Holiday Homes in South Portland

Our top choices for South Portland holiday homes

"Excellent in every way."

includes taxes & fees

8 Sept - 9 Sept

includes taxes & fees

9 Sept - 10 Sept

includes taxes & fees

27 Aug - 28 Aug

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

"Check in was simple. Quaint place. "

includes taxes & fees

27 Aug - 28 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! "

includes taxes & fees

3 Sept - 4 Sept

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

includes taxes & fees

1 Sept - 2 Sept

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

includes taxes & fees

2 Sept - 3 Sept

"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!"

includes taxes & fees

1 Sept - 2 Sept

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

includes taxes & fees

28 Aug - 29 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. "

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

includes taxes & fees

25 Sept - 26 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. "

includes taxes & fees

2 Sept - 3 Sept

"Perfect for our needs. Pictures don't do it justice, it is roomier than it looks. Would definitely book it again. "

includes taxes & fees

2 Sept - 3 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."

includes taxes & fees

9 Sept - 10 Sept