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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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, (76)
"Gorgeous and clean property. Can't wait to go again!"
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, (7)
"Booked for a weekend course, lovely spot, convenient location, and so close to everything you may need! Accommodating hosts, easy communication, and very responsive. "
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, (74)
"We loved everything about our stay! "
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)
"We were so pleased with how clean everything was, so very family friendly and so comfortable. Everything was great!"
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)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
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)
"Myself and my family get together. Every two years And stay at hills beach. We have been coming to this area since we were children and truly enjoy this location. This rental fit our needs perfectly with 3 different families all related And all with different needs. Our stay here allowed us to all be together and all have our own personal space. Lauren The owner was a great communicator and very accommodating to our needs. I absolutely recommend anyone who gets the chance to stay here."
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 truly enjoyed our stay at this lovely property. The owners made us feel so welcome and left a wonderful basket of breakfast and dinner goodies to enjoy. We can't say enough about this home. The house was immaculate and included a kitchen that was fully stocked with everything we could possibly need. The beds were super comfortable and the owners supplied all bed linens and towels. We wouldn't hesitate to recommend this property to family and friends. Thank you Susan and Steve for your...
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!"
The price is AED 654
AED 1,704 total
includes taxes & fees
8 Apr - 9 Apr
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 10,518 total
includes taxes & fees
8 May - 9 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, (109)
"Perfect location. Adorable house"
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)
"We enjoyed our brief stay"
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 layout, well-appointed and super walkable to Old Port, the great restos on Washington and the Eastern Promenade. Only downside was communication with Vacasa: they always answered but didn’t necessarily address the issue, ie I struggled with the electronic door lock, was leaving for the weekend, they said the owner would come address it but when I returned 3 days later it had been left unlocked all weekend. Unreliable WiFi & I work remotely. Several times had to work from cafes.beautifully...
The price is AED 588
AED 1,558 total
includes taxes & fees
8 Apr - 9 Apr
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
8.0 out of 10, Very Good, (1)
"It was very convenient. "
The price is AED 662
AED 1,996 total
includes taxes & fees
8 Apr - 9 Apr
Prime City Living Townhouse by RedAwning
Full sized home
Interior

Full sized home

9.6 out of 10, Exceptional, (24)
"The house is very clean, and it's very well situated. There are plenty of room in and out. Will come again."
The price is AED 826
AED 1,357 total
includes taxes & fees
9 Apr - 10 Apr
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)
"Comfortable, peaceful. Everything we needed for mussels, steamers and lobster Nice to have working dock in front of us for lobsters"
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

4.0 star property
9.6 out of 10, Exceptional, (51)
"Checkin might be a bit tricky if you’re parking - need to check in first by pulling up somewhere first before driving into the lot. But otherwise great property and very nice! Light sleepers should also bring earplugs as it gets loud with the outside noise"
The price is AED 574
AED 901 total
includes taxes & fees
27 Apr - 28 Apr
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, (103)
"Loved the property, location and views"
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 459
AED 1,005 total
includes taxes & fees
8 Apr - 9 Apr
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.