South Portland Holiday Homes from £247: Search Holiday Homes in South Portland

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.

1. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

14 Oct - 15 Oct

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 ♦ Perfect Location

West End

Susan d.

includes taxes & fees

19 Oct - 20 Oct

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

3. Tranquility between the Lakes & Sea

Westbrook

includes taxes & fees

1 Oct - 2 Oct

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

4. Spacious Portland Home + Parking

Parkside

Ellen M.

includes taxes & fees

29 Sept - 30 Sept

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

5. The 87th Townhome - Local Landmark

West End

Amy B.

includes taxes & fees

28 Oct - 29 Oct

A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

6. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

includes taxes & fees

28 Sept - 29 Sept

A living room with a sofa, a coffee table, and a vase on a windowsill.

7. Rare West End Home • Walk to Old Port, Harbor View

West End

Nikki W.

includes taxes & fees

1 Oct - 2 Oct

A bedroom with a bed, a window with curtains, a wall-mounted lamp, and a view of the outside.

8. Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi

Old Orchard Beach

includes taxes & fees

17 Oct - 18 Oct

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

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

Scarborough

Stuart R.

includes taxes & fees

1 Oct - 2 Oct

A two-story house with a balcony, a covered patio, and a fenced yard.

10. The Globe House on Munjoy Hill - Walk to Breweries

Munjoy Hill

Richard D.

includes taxes & fees

6 Oct - 7 Oct

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

11. Huge New Townhome 10mins from the Beach

Saco

Ellen L.

includes taxes & fees

28 Sept - 29 Sept

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

12. Adorable Seaside Cottage

Old Orchard Beach

Qi L.

includes taxes & fees

30 Sept - 1 Oct

A two-story house with a blue exterior, white railings, and a brick chimney.

13. OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA

Old Orchard Beach

Rachel A.

includes taxes & fees

30 Sept - 1 Oct

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

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

Buxton

Anonymous traveller

includes taxes & fees

28 Sept - 29 Sept

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

15. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

11 Oct - 12 Oct

An aerial view of a coastal residential area with beachfront properties, a main road, and a river.

16. Spacious 5BR Family Dream with Private Beach Access

Old Orchard Beach

Bradford P.

includes taxes & fees

28 Sept - 29 Sept

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.

17. 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

23 Oct - 24 Oct