Portland Vacation Home Rentals from CA $301: Search Top Private Vacation Homes for Rent

A cityscape with a prominent church steeple, various buildings, and lush green trees.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Portland vacation homes

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

1. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

CA $557 total

includes taxes & fees

Oct 20 - Oct 21

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

2. The 87th Townhome - Local Landmark

West End

Amy B.

CA $842 total

includes taxes & fees

Nov 2 - Nov 3

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.

3. 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.

CA $827 total

includes taxes & fees

Nov 6 - Nov 7

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.

CA $1,012 total

includes taxes & fees

Oct 12 - Oct 13

A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

5. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

CA $727 total

includes taxes & fees

Nov 3 - Nov 4

A two-story house with a covered porch, brick pathway, and a small garden area.

6. Charming West End Victorian

Parkside

CA $1,154 total

includes taxes & fees

Oct 13 - Oct 14

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

7. Willard Square Family Home

Willard Beach

David W.

CA $862 total

includes taxes & fees

Oct 14 - Oct 15

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

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

Munjoy Hill

Matt H.

CA $1,293 total

includes taxes & fees

Oct 28 - Oct 29

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

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

East Deering

Sally O.

CA $1,584 total

includes taxes & fees

Oct 12 - Oct 13

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

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

North Deering

Peter H.

CA $1,202 total

includes taxes & fees

Oct 18 - Oct 19

A living room with a fireplace, leather sofa, and a chandelier.

11. Charming Historic Estate | In-town location

West End

shelley w.

CA $3,765 total

includes taxes & fees

Nov 1 - Nov 2

A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

12. Whole Home | Sleeps 16 | Roof Deck|5 mins Downtown

Oakdale

"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "

Andy W.

CA $2,478 total

includes taxes & fees

Oct 15 - Oct 16