South Portland Holiday Houses

South Portland Holiday Homes
Maine
United States of America
Holiday Homes
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A lighthouse, rocky coastline, and a sunset over the ocean.

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Our top choices for South Portland holiday homes

A building named Willard Square with a storefront and a red vehicle parked outside.

A living room with a sofa, a coffee table, a lamp, and a chair.

A living room with a sofa, coffee table, and a ceiling fan.

A backyard with a wooden fence, a swing, and a lawn.

1. Willard Square Family Home

Willard Square Family Home

Willard Beach

9.8 out of 10, Exceptional, (13 reviews)

9.8/10

Exceptional

(13 reviews)

"Thoroughly enjoyed this house! "

David W.

The price is NZ$1,124

NZ$1,124

includes taxes & fees

22 Nov - 23 Nov

Willard Square Family Home

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

A living room with a sofa, coffee table, and a rug. There is a painting on the wall and a window with curtains.

A hotel room with a wooden floor, a bed with white linens, a small table, a ceiling fan, a wall-mounted light fixture, and a mirror.

A backyard with a white wooden fence, a small bush, a white wicker bench, and a stone wall in the background.

2. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

8.6 out of 10, Excellent, (64 reviews)

8.6/10

Excellent

(64 reviews)

"Nice place, good location and very responsive host. I would definitely stay again when in Portland."

Susan d.

The price is NZ$620

NZ$620

includes taxes & fees

2 Nov - 3 Nov

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

A two-story house with a green exterior and red trim, surrounded by trees with autumn leaves.

A staircase with a Christmas tree and a wooden chair.

A kitchen with wooden cabinets, a microwave, a stove, and a dining table with woven placemats.

A snow-covered landscape with a house and a tree.

3. Serenity between the lakes and seashore

Serenity between the lakes and seashore

Westbrook

9.8 out of 10, Exceptional, (33 reviews)

9.8/10

Exceptional

(33 reviews)

"Great place to stay"

richard a.

Serenity between the lakes and seashore

A window with a view of a snowy landscape and bare trees.

A dining area with a wooden table, chairs, a ceiling fan, and a vase of flowers.

A living room with a sofa, coffee table, wooden dining table, and chairs. There are windows with blinds, a ceiling fan, and wall-mounted artwork.

A house with Christmas lights forming shapes of a reindeer and a sleigh.

4. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea

Westbrook

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Great location. Very nice place."

Bernie G.

The price is NZ$556

NZ$556

includes taxes & fees

4 Nov - 5 Nov

Tranquility between the Lakes & Sea

A red building with a front door, a bay window, and a brick pathway.

A cozy living room with a wooden ceiling, a sofa, a coffee table, and a patterned rug.

A bedroom with a bed, two bedside tables with lamps, a dresser, and a door.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining area with a table and chairs.

5. Spacious Portland Home + Parking

Spacious Portland Home + Parking

Parkside

8.6 out of 10, Excellent, (4 reviews)

8.6/10

Excellent

(4 reviews)

"we used the house has home base for several outings in Portland. Great location and easy parking."

Ellen M.

The price is NZ$1,059

NZ$1,059

includes taxes & fees

5 Nov - 6 Nov

Spacious Portland Home + Parking

A two-story brick building with a front porch, a black door, and a window with a white frame.

A living room with a sofa set, a coffee table, a bookshelf, and a large plant.

A spacious kitchen with a dining table, two windows with curtains, a fireplace, and a chandelier.

A spacious living room with a sofa, armchairs, a coffee table, and a TV. There is a staircase leading to another level.

6. The 87th Townhome by Everrow

The 87th Townhome by Everrow

West End

9.6 out of 10, Exceptional, (11 reviews)

9.6/10

Exceptional

(11 reviews)

"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"

Amy B.

The price is NZ$967

NZ$967

includes taxes & fees

30 Nov - 1 Dec

The 87th Townhome by Everrow

A wooden covered porch with a green door, potted plants, and a red watering can.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden countertop.

A two-story house with a front porch, a picket fence, and a tree in the foreground.

A residential area with a paved patio, outdoor seating, and a small garden.

7. Charming West End Victorian

Charming West End Victorian

Parkside

Charming West End Victorian

A living room with a sofa, armchair, ottoman, and a colorful geometric rug.

An outdoor patio with a table and chairs, a small round table with a plant, and a bamboo fence.

A bedroom with a bed, a nightstand, a red side table, a window with curtains, and a wall with a leaf pattern.

A modern kitchen with a dining area, featuring a table set for four, red chairs, and pendant lighting.

8. Modern & Sunny East End House.

Modern & Sunny East End House.

Munjoy Hill

10.0 out of 10, Exceptional, (51 reviews)

10/10

Exceptional

(51 reviews)

"Perfect stay for a quick trip to Portland! "

stacey p.

The price is NZ$919

NZ$919

includes taxes & fees

30 Nov - 1 Dec

Modern & Sunny East End House.

A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

A modern kitchen with a bar area, white cabinetry, and a skylight.

A covered swimming pool with glass walls, benches, and a hot tub area.

A modern kitchen with white cabinetry, a granite countertop, a stainless steel refrigerator, and a built-in oven.

9. 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, (17 reviews)

10/10

Exceptional

(17 reviews)

"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."

Stuart R.

The price is NZ$1,092

NZ$1,092

includes taxes & fees

9 Nov - 10 Nov

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

A light blue door with a numerical address sign, a doormat, and two wall-mounted lights.

A room with a fireplace, two leather armchairs with throw blankets, a rug, and a large animal hide on the floor.

A modern kitchen with white cabinets, a black stovetop, and a red pot.

A wooden deck with a wicker sofa, a rocking chair, and a small table.

10. Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

Biddeford

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This little house was absolutely charming! The owners were very accommodating and flexible with our dates and last minute booking. The house is incredibly cozy and the outdoor porch was a big hit. The location of this house is also amazing as you have access to the ocean, marsh and a beautiful pond. E would love to return with our grandkids who would love it! Thank you Shannon and Jim for sharing your special house with us!"

Allison B.

The price is NZ$1,082

NZ$1,082

includes taxes & fees

2 Nov - 3 Nov

Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

A modern living room with a fireplace, a coffee table, and a sofa. There are potted plants on a shelf and a framed botanical print on the wall.

A hallway leading to a kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and an oven.

A hallway with a black door, wooden shelves, and a staircase.

11. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.

Munjoy Hill

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Great space for our needs: three generations for a graduation weekend!"

Matt H.

The price is NZ$1,518

NZ$1,518

includes taxes & fees

4 Nov - 5 Nov

Spacious 4-bedroom house located in the heart of Portland, ME.

A narrow hallway with white walls, a blue carpet, and a door leading outside.

A living room with a brown leather sofa, a framed picture on the wall, a staircase with wooden steps, and a window with blinds.

A two-story house with a front porch, a mailbox, and an American flag.

A cozy living room with a leather sofa, a white armchair, a small wooden table with a vase, and a TV on a white cabinet.

12. Seaside Retreat by Everrow

Seaside Retreat by Everrow

Old Orchard Beach

8.4 out of 10, Very good, (6 reviews)

8.4/10

Very good

(6 reviews)

"Overall nice small place, owner responded quickly to issues. "

Qi L.

The price is NZ$738

NZ$738

includes taxes & fees

2 Nov - 3 Nov

Seaside Retreat by Everrow

A living room with a sofa, armchair, wooden coffee table, and a potted plant.

A dining area with a wooden table and chairs, a potted plant, and artwork on the walls.

A kitchen with wooden cabinets, a central island, bar stools, a refrigerator, and pendant lighting.

A living room with wooden beams, a TV, a sofa, a coffee table, and a rug.

13. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport

Freeport

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Great property well kept and close to everything we wanted to do"

boodu

Fully Updated Airy Historic Home in South Freeport

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

A bedroom with two beds, a nightstand, and a window with blinds.

A laundry room with a front-loading washer and dryer, wooden flooring, and a white door.

A compact kitchen with a refrigerator, microwave, coffee maker, and a sink.

14. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood

Freeport

The price is NZ$670

NZ$670

includes taxes & fees

2 Nov - 3 Nov

Quiet Spot in lovely Freeport neighborhood

A living room with a grey sofa, two patterned armchairs, a round wicker coffee table, and a flat-screen TV mounted on the wall.

A modern kitchen with wooden cabinets, a central island, and a dining area with a black table and chairs.

A spacious living room with hardwood flooring, a grey sofa with a blue pillow, a wooden bench, and a staircase with white railings.

A kitchen with wooden cabinets, a stainless steel stove, a dishwasher, and a window with a view of greenery.

15. Townhome: 10 Min to Beach by Everrow

Townhome: 10 Min to Beach by Everrow

Saco

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"The property is very close to I 95 making it very convenient to commute to portland. It is close to a grocery store. It was clean and the pictures were accurate. Our family of 6 had a nice stay."

Krista B.

The price is NZ$812

NZ$812

includes taxes & fees

2 Nov - 3 Nov

Townhome: 10 Min to Beach by Everrow

A miniature golf course with two flags, a putting green, and a golf club.

A kitchen with wooden cabinets, a white refrigerator, a microwave, and a stove.

A bedroom with a bed, a nightstand, a wall clock, a window with curtains, and a painting on the wall.

A dining area with a table, chairs, a ceiling fan, and a large mirror on the wall.

16. Cozy Beach Cottage | Fire Pit & Yard

Cozy Beach Cottage | Fire Pit & Yard

Old Orchard Beach

Cozy Beach Cottage | Fire Pit & Yard

A courtyard with outdoor seating, a staircase leading to a building, and blooming trees.

Great views from the loft, which also has 2 queen beds plus a queen Luonto sofabed.

17. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space

Downtown Portland

The price is NZ$2,149

NZ$2,149

includes taxes & fees

30 Nov - 1 Dec

Steps to Old Port, balcony, private outdoor space

A covered wooden deck with a view of a building's exterior.

A bedroom with a bed, a nightstand, a wooden dresser, a painting on the wall, and a closet.

A modern kitchen with a bar area, a dining set, and a living room with a TV.

A kitchen with white cabinets, a granite countertop, a wooden island with bar stools, and a dishwasher.

18. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Buxton

7.6 out of 10, Good, (4 reviews)

7.6/10

Good

(4 reviews)

"Overall all nice stay. Thank you"

Hope T.

The price is NZ$571

NZ$571

includes taxes & fees

7 Nov - 8 Nov

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

A deck with a barbecue, a table, and a chair.

A modern kitchen with white cabinets, a wooden dining table, and chairs. There are two windows with curtains, a potted plant, and artwork on the wall.

A second look at the porch and its connection to the main living area.

A residential area with houses, a driveway, and a fenced yard.

19. Walk to Beach | Sleeps 10 | Porch

Walk to Beach | Sleeps 10 | Porch

Old Orchard Beach

Walk to Beach | Sleeps 10 | Porch

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

A window with a view of a backyard, a patio area, and a large tree.

A cozy living room with a fireplace, a television mounted above it, and a sign indicating the location as Portland, Maine.

A wooden dining table with benches, a hanging light fixture, and wooden cabinets with glass doors.

20. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering

10.0 out of 10, Exceptional, (85 reviews)

10/10

Exceptional

(85 reviews)

"Absolutely perfect rental!Great location with an amazing view!"

Mike G.

The price is NZ$1,855

NZ$1,855

includes taxes & fees

2 Nov - 3 Nov

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

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

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent

"Great stay"

Adam 1-night trip

Posted 2 hours ago

Spark by Hilton Portland Airport Maine Mall

Comfort Inn South Portland Airport

8/10 Good

"Rooms are spacious and the bed is comfortable. The outlets were not all working. Went down for breakfast but most of the food was gone before 9:30am. The lady that was working evening shift was very friendly when we checked in. I would stay again for the price we paid."

Amy 1-night trip

Posted 2 hours ago

Comfort Inn South Portland Airport

Holiday Inn Express Hotel & Suites South Portland by IHG

10/10 Excellent

"Receptionist was excellent( black lady)"

Desire 3-night trip

Posted 3 hours ago

Holiday Inn Express Hotel & Suites South Portland by IHG

Clarion Pointe South Portland

10/10 Excellent

"it was an enjoyable visit."

James 3-night trip

Posted 4 hours ago

Clarion Pointe South Portland

Portland Harbor Hotel

10/10 Excellent

"Perfect location, beautiful hotel! Hotel was very clean and upscale. With a common coffee/tea/snack bar on each floor."

Jennifer 1-night trip

Posted 1 day ago

Portland Harbor Hotel

Courtyard by Marriott Portland Airport

10/10 Excellent

"I am very impressed with all staff, especially the front desk staff. (The Asian lady who was on duty Thursday and Friday Oct 29 and 30)."

Mai 1-night trip

Posted 1 day ago

Courtyard by Marriott Portland Airport

TownePlace Suites by Marriott Portland Airport ME

10/10 Excellent

"Property is new and very comfortable. Staff seemed great. Breakfast options are very limited, so so."

Kathleen 1-night trip

Posted 2 days ago

TownePlace Suites by Marriott Portland Airport ME

Long Creek Hotel by IHG

10/10 Excellent

"Very nice and quiet."

Amanda 2-night trip

Posted 6 days ago

Long Creek Hotel by IHG

Find out more about South Portland

South Portland Holiday Homes information

Number of reviews	290
Accommodation	652 Holiday Homes
Lowest Price	NZ$556
Highest Price	NZ$1,855

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in South Portland on Expedia.com

Holiday Homes in South Portland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Portland holiday homes

1. Willard Square Family Home

2. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

3. Serenity between the lakes and seashore

4. Tranquility between the Lakes & Sea

5. Spacious Portland Home + Parking

6. The 87th Townhome by Everrow

7. Charming West End Victorian

8. Modern & Sunny East End House.

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

10. Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

11. Spacious 4-bedroom house located in the heart of Portland, ME.

12. Seaside Retreat by Everrow

13. Fully Updated Airy Historic Home in South Freeport

14. Quiet Spot in lovely Freeport neighborhood

15. Townhome: 10 Min to Beach by Everrow

16. Cozy Beach Cottage | Fire Pit & Yard

17. Steps to Old Port, balcony, private outdoor space

18. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

19. Walk to Beach | Sleeps 10 | Porch

20. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Find holiday rentals that suit your style

Top South Portland Hotel Reviews

Spark by Hilton Portland Airport Maine Mall

Find out more about South Portland

South Portland Holiday Homes information

Explore a world of travel with Expedia