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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for South Portland holiday homes

Microwave, oven, stovetop, dishwasher

Toast to 2026! Free Champagne for all Jan / Feb Bookings

Toast to 2026! Free Champagne for all Jan / Feb Bookings
South Portland
10.0 out of 10, Exceptional, (4 reviews)
"The house was very nice and had great accommodations for our group. The kitchen and living room was very accommodating for meals and hangouts and we were close to all of the activities we were looking to do"
United States
Justin R.
Toast to 2026! Free Champagne for all Jan / Feb Bookings
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is £379
includes taxes & fees
22 Apr - 23 Apr
Modern Getaway by the Sea
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 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 £408
includes taxes & fees
31 Mar - 1 Apr
Willard Square Family Home
Interior

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, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is £181
includes taxes & fees
9 Apr - 10 Apr
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Living area

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Old Orchard Beach
9.4 out of 10, Exceptional, (15 reviews)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is £359
includes taxes & fees
30 Mar - 31 Mar
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Beach nearby, sun-loungers, beach towels

Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean
Old Orchard Beach
10.0 out of 10, Exceptional, (58 reviews)
"House was very nice, plenty of room, and accommodating."
United States
Joey S.
The price is £357
includes taxes & fees
29 Mar - 30 Mar
Beach House ∆ Prime Location ∆ Steps to the Ocean
Outdoor dining

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, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is £274
includes taxes & fees
29 Mar - 30 Mar
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is £274
includes taxes & fees
30 Mar - 31 Mar
Full sized home
3 bedrooms, desk, iron/ironing board, travel cot

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (6 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
The price is £297
includes taxes & fees
29 Mar - 30 Mar
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is £318
includes taxes & fees
16 Apr - 17 Apr
Mere Point Sunrise Views at Eastern Shore!
Dining

Seaglass Cottage by Bayley Vacation Rentals

Seaglass Cottage by Bayley Vacation Rentals
Old Orchard Beach
Seaglass Cottage by Bayley Vacation Rentals
Outdoor dining

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The price is £415
includes taxes & fees
22 Apr - 23 Apr
The Globe House on Munjoy Hill - Walk to Breweries
Smart TV

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 £370
includes taxes & fees
29 Mar - 30 Mar
Huge New Townhome 10mins from the Beach
Beach nearby

Charming Victorian beach house 5 bedrooms. 50 steps to the beach

Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Old Orchard Beach
9.6 out of 10, Exceptional, (18 reviews)
"We had a great time and it’s an awesome place. Can’t wait to rebook for next year. "
United States
Robert D.
The price is £646
includes taxes & fees
29 Mar - 30 Mar
Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Interior

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (12 reviews)
"We had a fantastic stay. Alexa was a wonderful host!"
United States
Desmond L.
The price is £375
includes taxes & fees
1 Apr - 2 Apr
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Outdoor dining

Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub

Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub
Old Orchard Beach
9.0 out of 10, Wonderful, (25 reviews)
"We loved our stay at the Bliss Beach House! The sky deck provided a huge area to relax, enjoy the view and even had a hot tub. The kitchen was spacious with plenty of seating and had everything we needed for our stay. Jason was great with communication before and during our stay. "
United States
Laurie O.
The price is £467
includes taxes & fees
29 Mar - 30 Mar
Bliss Beach House ♦ Vast Ocean Views ♦ Skydeck ♦ Private Hot Tub
1 bedroom, Internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is £208
includes taxes & fees
22 Apr - 23 Apr
Charming 1-bedroom ADU in wonderful Portland neighborhood
Property grounds

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is £413
includes taxes & fees
22 Apr - 23 Apr
Modern Cottage with Peeks of Ocean Views
Exterior

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.0 out of 10, Wonderful, (4 reviews)
"Great location"
United States
Mark J.
The price is £333
includes taxes & fees
6 Apr - 7 Apr
The 87th Townhome - Local Landmark
Outdoor dining

Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
9.0 out of 10, Wonderful, (2 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 £477
includes taxes & fees
1 Apr - 2 Apr
Spacious Portland Home + Parking
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Easy check in and valet. Room was clean. While the sauna, Steam and hot tub were nice, if you look too close it doesn't appear to get regular cleaning(floors were not very clean in hot tub area)"
Lanandra 2-night trip
Posted 1 hour ago
Portland Regency Hotel & Spa

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews
393
Accommodation
732 Holiday Homes
Lowest Price
£181
Highest Price
£646