South Portland Holiday House Rentals from AU$464: Search Holiday Homes

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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.

1. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

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

2. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

West End

Susan d.

includes taxes & fees

9 Nov - 10 Nov

An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

3. Spacious Portland Home + Parking

Parkside

Ellen M.

includes taxes & fees

9 Nov - 10 Nov

A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

4. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Munjoy Hill

"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...

Maris P.

includes taxes & fees

11 Nov - 12 Nov

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

5. Charming West End Victorian

Parkside

includes taxes & fees

1 Dec - 2 Dec

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

6. The 87th Townhome by Everrow

West End

Amy B.

includes taxes & fees

9 Nov - 10 Nov

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

7. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

9 Nov - 10 Nov

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

8. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

includes taxes & fees

11 Nov - 12 Nov

A storefront with the sign 'OYSTERS' and a 'RAW BAR' sign above the entrance. There are outdoor seating areas with tables and chairs.

9. Modern & Sunny East End House.

Munjoy Hill

stacey p.

includes taxes & fees

9 Nov - 10 Nov

A deck with a grill, chairs, and a table.

10. • Quiet 3BR Home Close to Biddeford Beaches

Biddeford

"This place was okay- it served our needs. A few complaints- generally a dingy smell throughout the house, felt damp. The bathroom shower curtain has no liner so the curtain itself was very moldy. The grass wasnt mowed so I worried about ticks. The water tasted a little musty too but maybe thats just a Maine thing? Also the communication was pretty terrible with both the vrbo host and the property management company and I had a lot of trouble contacting them and getting the receipts I needed....

Ellen B.

includes taxes & fees

15 Nov - 16 Nov

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

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

Scarborough

Stuart R.

includes taxes & fees

9 Nov - 10 Nov

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

12. Seaside Retreat by Everrow

Old Orchard Beach

Qi L.

includes taxes & fees

9 Nov - 10 Nov

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

13. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

includes taxes & fees

10 Nov - 11 Nov

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

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

Munjoy Hill

Matt H.

includes taxes & fees

9 Nov - 10 Nov

A covered porch with a view of a lake and trees.

15. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

includes taxes & fees

16 Nov - 17 Nov

A dining area with a long wooden table, six chairs, and a bench. There are large windows with curtains, a plant, and a view into another room.

16. New and Spacious Family Home Close to Sebago Lake

Standish

A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

17. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

North Deering

Patrick J.

includes taxes & fees

22 Nov - 23 Nov

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

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

East Deering

Mike G.

includes taxes & fees

12 Nov - 13 Nov

A beach with footprints, a person standing, and birds on the sand.

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

Buxton

Hope T.

includes taxes & fees

9 Nov - 10 Nov

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

20. Townhome: 10 Min to Beach by Everrow

Saco

Krista B.

includes taxes & fees

13 Nov - 14 Nov

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Learn more about South Portland

Stroll along Willard Beach's sandy shores before exploring the charming Bug Light lighthouse park. Foodies can savour local flavours at welcoming restaurants, while shoppers browse the expansive Maine Mall for treasures.

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