South Portland Holiday Houses

South Portland Holiday Homes
Maine
United States of America
Holiday Homes
Expedia.co.nz

Hotels in South Portland Holiday Rentals in South Portland Flights to South Portland South Portland Car Hire South Portland Holiday Packages

Portland Harbor aerial view from Eastern Promenade in East End, city of Portland, Maine ME, USA.

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Our top choices for South Portland holiday homes

Holiday Home in South Portland

Modern Getaway by the Sea

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Had a nice stay! House was great."

Karen T.

The price is NZ$855

NZ$855

includes taxes & fees

19 Mar - 20 Mar

Modern Getaway by the Sea

3 bedrooms, iron/ironing board, travel cot, WiFi

Holiday Home in Willard Beach

Willard Square Family Home

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"Thoroughly enjoyed this house! "

David W.

The price is NZ$949

NZ$949

includes taxes & fees

31 Mar - 1 Apr

Willard Square Family Home

Holiday Home in South Portland

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

10.0 out of 10, Exceptional, (4 reviews)

10/10

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"

Justin R.

The price is NZ$1,063

NZ$1,063

includes taxes & fees

5 Apr - 6 Apr

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

2 bedrooms, blackout curtains, iron/ironing board, free WiFi

Holiday Home in West End

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.4 out of 10, Very good, (59 reviews)

8.4/10

Very good

(59 reviews)

"Nice place. Good location."

Rob M.

The price is NZ$436

NZ$436

includes taxes & fees

19 Mar - 20 Mar

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Beach nearby, sun-loungers, beach towels

Holiday Home in Old Orchard Beach

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (57 reviews)

10/10

Exceptional

(57 reviews)

"House was very nice, plenty of room, and accommodating."

Joey S.

The price is NZ$812

NZ$812

includes taxes & fees

18 Mar - 19 Mar

Beach House ∆ Prime Location ∆ Steps to the Ocean

Holiday Home in Harpswell

Full sized home

9.8 out of 10, Exceptional, (51 reviews)

9.8/10

Exceptional

(51 reviews)

"Super clean and lovely place to stay! Highly recommend!"

Evan B.

The price is NZ$619

NZ$619

includes taxes & fees

18 Mar - 19 Mar

Full sized home

Holiday Home in Munjoy Hill

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Perfect stay for a quick trip to Portland! "

stacey p.

The price is NZ$555

NZ$555

includes taxes & fees

19 Mar - 20 Mar

Modern & Sunny House Steps from the Promenade. Private Parking!

Holiday Home in West End

The 87th Townhome - Local Landmark

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"Great location"

Mark J.

The price is NZ$603

NZ$603

includes taxes & fees

18 Mar - 19 Mar

The 87th Townhome - Local Landmark

6 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Old Orchard Beach

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

9.4 out of 10, Exceptional, (15 reviews)

9.4/10

Exceptional

(15 reviews)

"Awesome place lots of room very much enjoyed "

Anthony M.

The price is NZ$870

NZ$870

includes taxes & fees

30 Mar - 31 Mar

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

3 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Old Orchard Beach

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

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"We had a wonderful stay at Garett and Sophia’s beautiful Maine home! From booking to check in and check out Garett was extremely helpful with any questions. The property was just as described and perfect for our family of 3! Would highly recommend!"

Taylor D.

The price is NZ$598

NZ$598

includes taxes & fees

22 Mar - 23 Mar

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

Holiday Home in Old Orchard Beach

The Dollhouse

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"Wonderful stay for a small bachelorette party! Right squeeze with 7 girls but great to have the place already decorated. Very close to the pier and lots of stores, restaurants, and places to go around. Host was very friendly and accommodating, answered questions and was flexible with any of our needs!"

Margaret D.

The price is NZ$1,227

NZ$1,227

includes taxes & fees

18 Mar - 19 Mar

The Dollhouse

Holiday Home in Cape Elizabeth

Modern Cottage with Peeks of Ocean Views

10.0 out of 10, Exceptional, (1 review)

10/10

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! "

Christina S.

The price is NZ$753

NZ$753

includes taxes & fees

2 Apr - 3 Apr

Modern Cottage with Peeks of Ocean Views

Holiday Home in Old Orchard Beach

Seaglass Cottage by Bayley Vacation Rentals

The price is NZ$2,012

NZ$2,012

includes taxes & fees

5 Apr - 6 Apr

Seaglass Cottage by Bayley Vacation Rentals

Holiday Home in Old Orchard Beach

Spacious 5BR Family Dream with Private Beach Access

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"Had a great stay. Plenty of amenities that made it nice since it's the winter months. "

Bradford P.

The price is NZ$891

NZ$891

includes taxes & fees

18 Mar - 19 Mar

Spacious 5BR Family Dream with Private Beach Access

Holiday Home in Buxton

Victorian Farmhouse | Walk to Saco River

The price is NZ$647

NZ$647

includes taxes & fees

18 Mar - 19 Mar

Victorian Farmhouse | Walk to Saco River

Holiday Home in Back Cove

Charming 1-bedroom ADU in wonderful Portland neighborhood

The price is NZ$471

NZ$471

includes taxes & fees

18 Mar - 19 Mar

Charming 1-bedroom ADU in wonderful Portland neighborhood

Holiday Home in Biddeford

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"We have stayed three times and will be back"

Michael W.

The price is NZ$1,107

NZ$1,107

includes taxes & fees

18 Mar - 19 Mar

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland

Holiday Home in Old Orchard Beach

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

9.6 out of 10, Exceptional, (18 reviews)

9.6/10

Exceptional

(18 reviews)

"We had a great time and it’s an awesome place. Can’t wait to rebook for next year. "

Robert D.

The price is NZ$1,442

NZ$1,442

includes taxes & fees

29 Mar - 30 Mar

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

Holiday Home in Old Orchard Beach

The Sea Gaze - 5BR with Beach Path

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Beautiful house and great location "

Nicole K.

The price is NZ$917

NZ$917

includes taxes & fees

22 Mar - 23 Mar

The Sea Gaze - 5BR with Beach Path

Holiday Home in Biddeford

A historic treasure in Southern Maine, very unique and spacious

10.0 out of 10, Exceptional, (44 reviews)

10/10

Exceptional

(44 reviews)

"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "

Jeanne C.

The price is NZ$1,674

NZ$1,674

includes taxes & fees

18 Mar - 19 Mar

A historic treasure in Southern Maine, very unique and spacious

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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