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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 730 Vacation Homes in South Portland with updated reviews, rates, and availability.

Cute House -2 Blocks from Beach
Sun loungers, beach towels

Cute House -2 Blocks from Beach

9.4 out of 10, Exceptional, (24)
"Nice place with two bedrooms and a full kitchen. While it looks small from the outside, it’s is nicely roomy inside. "
Cute House -2 Blocks from Beach
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, table tennis, books

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very Good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (77)
"Great historic house in a terrific location. "
The Globe House on Munjoy Hill - Walk to Breweries
Elegant Orchard Retreat: Generous Yard & Patio
Beach

Elegant Orchard Retreat: Generous Yard & Patio

2.0 star property
9.0 out of 10, Wonderful, (8)
"Clean, easy check-in, good location with a lot of amenities provided including a well-equipped kitchen. We stayed off-season but this would be a lovely place to stay during the peak season as it's close to the beach/attractions but also private with a nice sized fenced yard."
Elegant Orchard Retreat: Generous Yard & Patio
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House
Maine Cottage
Property grounds

Maine Cottage

9.8 out of 10, Exceptional, (75)
"Second time staying at this property and will definitely stay again !!! "
Maine Cottage
The Boathouse Cottage is a beachfront family retreat
Terrace/patio

The Boathouse Cottage is a beachfront family retreat

9.8 out of 10, Exceptional, (70)
"Wonderful spot to gather with family not far from the beach"
The Boathouse Cottage is a beachfront family retreat
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"We had a great stay! Amazing weather and plenty of lobster."
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Private Lakefront Estate with 180 Degree Views
Property grounds

Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views
Oceanfront Home | Beach Access | Deck + Ping Pong
Offices

Oceanfront Home | Beach Access | Deck + Ping Pong

Oceanfront Home | Beach Access | Deck + Ping Pong
One of kind Ocean Front Compound with private beach!
Interior

One of kind Ocean Front Compound with private beach!

9.2 out of 10, Wonderful, (12)
"Enjoyed our stay"
One of kind Ocean Front Compound with private beach!
4BR, 2 level, comfortable House In Kennebunkport/Cape Porpoise Maine.
Beach

4BR, 2 level, comfortable House In Kennebunkport/Cape Porpoise Maine.

10.0 out of 10, Exceptional, (26)
"We had a wonderful trip. The house is very room and in a great location. So much to do so close by. I would definitely recommend this place to others"
4BR, 2 level, comfortable House In Kennebunkport/Cape Porpoise Maine.
Spacious Country Home Freeport, Only 5 min to LL Bean!
Interior

Spacious Country Home Freeport, Only 5 min to LL Bean!

9.8 out of 10, Exceptional, (12)
"We loved everything about this place. Beautiful, large home, plenty of room for 8 adults and 2 children. Large dining room for meals and family game time. So close to Freeport and all the shopping. Very clean, and the home has everything we needed. We can’t wait to go again!"
Spacious Country Home Freeport, Only 5 min to LL Bean!
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard
Beach

Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

The price is AED 5,693
AED 10,409 total
includes taxes & fees
9 May - 10 May
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard
Quintessential Maine Beach Cottage
Property grounds

Quintessential Maine Beach Cottage

10.0 out of 10, Exceptional, (111)
"Comfortable and close to beach and other fun sites."
Quintessential Maine Beach Cottage
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Beach nearby

Dog-friendly cottage with deck & porch - walk to the beach, pier & town

8.2 out of 10, Very Good, (12)
"Dog friendly."
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (60)
"Great location, walkable to everything we wanted to do in Portland"
The price is AED 588
AED 1,538 total
includes taxes & fees
11 May - 12 May
Elegant condo - walk to Portland's best restaurants & Old Port
Prime City Living Townhouse by RedAwning
Fridge, microwave, oven, dishwasher

Prime City Living Townhouse by RedAwning

2.0 star property
9.0 out of 10, Wonderful, (2)
"It was very convenient. "
The price is AED 678
AED 1,989 total
includes taxes & fees
12 May - 13 May
Prime City Living Townhouse by RedAwning
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (26)
"This property was as described and it felt like we were staying at a family member’s cozy house. The towels were thick, the beds were comfortable, and the kitchen had everything we needed."
The price is AED 826
AED 1,373 total
includes taxes & fees
12 May - 13 May
Full sized home
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Terrace/patio

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.8 out of 10, Exceptional, (59)
"We had our wedding party stay at this property for our wedding at live well farm. It was beautiful and everyone enjoyed their stay. "
Beautiful house on the Harpswell Peninsula over looking Casco Bay
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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Other property types in South Portland

The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (58)
"Great hotel"
The price is AED 909
AED 1,266 total
includes taxes & fees
13 May - 14 May
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (105)
"Lovely, clean & great location!"
Gorgeous ocean-front home with stunning beach views
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (124)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is AED 918
AED 1,573 total
includes taxes & fees
19 May - 20 May
Oceanfront Condo! Spectacular Views From Private Large Balcony
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.