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Portland Vacation Rentals

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Vacation Rentals in Portland

Downtown Old Port Luxury Penthouse. 25% Discounts

Downtown Old Port Luxury Penthouse. 25% Discounts

Portland, ME

Located in Downtown Portland, this romantic condo building is within a 10-minute walk of Casco Bay Lines Ferry Terminal and Cross Insurance Arena. Merrill Auditorium ...

4.7/5Exceptional! (12 reviews)
Can't get a better location!

"Beautiful Loft Downtown, Walking distance to the best amenities in Portland!!! We loved everything about the unit and the property manager was a pleasure to work with. I will definitely stay here again!"…"

Reviewed on Dec. 16, 2020

Downtown Old Port Luxury Penthouse. 25% Discounts
121B Portland Ave Cabin - 1 Br cabin by RedAwning

121B Portland Ave Cabin - 1 Br cabin by RedAwning

3.5 out of 5
121B Portland Ave, Old Orchard Beach, ME

Situated in Old Orchard Beach, this cabin is within 1 mi (2 km) of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club and Monkey Trunks Extreme ...

4/5Very Good! (1 review)
Cute guesthouse w/full kitchen in lovely Maine

"This is a very cute, cozy little place. Full size oven and fridge. Great location with local grocery nearby and larger retailers and restaurants a 15 minute drive away. Cons: Bed was a full, not a queen (as larger people we did not sleep well as a result), the "cabin" is really a cute guesthouse ..."…"

Reviewed on Nov. 5, 2020

121B Portland Ave Cabin - 1 Br cabin by RedAwning
The Cottages at Cabot Cove

The Cottages at Cabot Cove

3.5 out of 5
7 South Main Street, Kennebunkport, ME

Located in the heart of Kennebunkport, this cottage is within a 15-minute walk of Kennebunkport Village Green, Mast Cove Galleries, and W. Robert Paine Gallery. ...

4.6/5Wonderful! (19 reviews)

"great location; very private and quiet; cottage amenities very quaint and comfortable"…"

Reviewed on May 30, 2019

The Cottages at Cabot Cove
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Oceanfront Condo!!!! Steps to 7 Mile Beach, Steps to Downtown Old Orchard Beach

Oceanfront Condo!!!! Steps to 7 Mile Beach, Steps to Downtown Old Orchard Beach

Old Orchard Beach, ME
The price is CA $121 per night from Jan 24 to Jan 25

Nestled on the beach, this Old Orchard Beach condo building is within a 10-minute walk of Old Orchard Beach and Old Orchard Beach Pier. Ferry Beach and Dunegrass ...

4.8/5Exceptional! (74 reviews)
Sunrise at your door!

"Clean condo right on the beach."…"

Reviewed on Jan. 10, 2021

Oceanfront Condo!!!! Steps to 7 Mile Beach, Steps to Downtown Old Orchard Beach
Beach Front Condo on the Beach / Updated / Immaculately Clean

Beach Front Condo on the Beach / Updated / Immaculately Clean

Old Orchard Beach, ME

Situated on the beach, this historic condo building is within a 15-minute walk of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club is 2.1 mi ...

4.9/5Exceptional! (9 reviews)
The perfect vacation spot

"This place was the perfect vacation spot. #1 you can’t beat the location. It’s right on the beach and super close to a Grocery store and Walgreens. You have your own parking space, which is also a little perk I loved. #2 The place was very clean, super cute, and the perfect size for my boyfriend ..."…"

Reviewed on Sep. 20, 2020

Beach Front Condo on the Beach / Updated / Immaculately Clean
New Listing! Updated Getaway - Near Beach & Dining 2 Bedroom Home

New Listing! Updated Getaway - Near Beach & Dining 2 Bedroom Home

3.5 out of 5
177 Temple Ave, Old Orchard Beach, ME

This family-friendly Old Orchard Beach vacation home is within 2 mi (3 km) of Old Orchard Beach and Harmon Historical Museum. Old Orchard Beach Pier is 2 mi ...

New Listing! Updated Getaway - Near Beach & Dining 2 Bedroom Home
Light-filled Studio Condo in the Center of Downtown-walk to Dining/shopping!

Light-filled Studio Condo in the Center of Downtown-walk to Dining/shopping!

Kennebunkport, ME
The price is CA $94 per night from Jan 26 to Jan 27

Located in the heart of Kennebunkport, this historic vacation home is steps from Mast Cove Galleries, First Families Kennebunkport Museum, and Dock Square. W. ...

5/5Exceptional! (1 review)
Great location

"Great location. My only complaint is the parking is on the opposite side of the entrance of the building. The room was very spacious and clean. We would rent again."…"

Reviewed on Oct. 29, 2020

Light-filled Studio Condo in the Center of Downtown-walk to Dining/shopping!
84 Main by Capital Vacations

84 Main by Capital Vacations

4 out of 5
84 Main Street, Kennebunk, ME

Situated by the ocean, this condo building is within a 5-minute walk of Brick Store Museum and Kennebunk Free Library. Gardens at Historic Wallingford Hall and ...

4.9/5Exceptional! (31 reviews)
Terrific Location

"Stay in the heart of Kennebunk, easy drive to KBP or the beaches. Clean, safe, spacious."…"

Reviewed on Dec. 14, 2020

84 Main by Capital Vacations
Little Miss Cottages

Little Miss Cottages

2.5 out of 5
173 East Grand Ave, Old Orchard Beach, ME

Located in the heart of Old Orchard Beach, this cottage is within 1 mi (2 km) of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club is 2.3 mi ...

3.8/5Good! (37 reviews)

"Great place to stay! Very clean, and comfortable, and the staff is exceptionally attentive and polite!! Not our first stay, and certainly won’t be our last!"…"

Reviewed on Jul. 27, 2020

Little Miss Cottages
Sweet Suite near beach in quiet wooded setting.

Sweet Suite near beach in quiet wooded setting.

Kennebunk, ME
The price is CA $121 per night from Jan 19 to Jan 20

Situated by the ocean, this apartment building is 0.6 mi (1 km) from Kennebunk Dog Park and within 3 mi (5 km) of Wedding Cake House and Brick Store Museum. ...

5/5Exceptional! (23 reviews)
Private Suite

"Very comfy and cozy! Private entrance and private from the entire house and all around just enjoyed our stay!"…"

Reviewed on Nov. 3, 2020

Sweet Suite near beach in quiet wooded setting.
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Portland, ME
The price is CA $150 per night from Jan 19 to Jan 20

This family-friendly Portland apartment building is located by the ocean, within a 10-minute walk of Eastern Promenade and Portland Observatory. Cross Insurance ...

4.9/5Exceptional! (18 reviews)
Cozy attic apartment

"We loved this sweet little place! It had every little thing we might need, and was just so comfortable and lovely. Very happy we chose to stay here. We ended up doing more driving than walking because of the weather, but it would have been an easy walk to a lot of what we were doing. My only advice, ..."…"

Reviewed on Oct. 5, 2020

Adorable Portland getaway on the Eastern Promenade
Grand Victorian, Luxury Condo, Top Floor Unit With Ocean Views, NO fees

Grand Victorian, Luxury Condo, Top Floor Unit With Ocean Views, NO fees

Old Orchard Beach, ME

Located in the heart of Old Orchard Beach, this condo building is steps from Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club and Ferry Beach ...

4.8/5Exceptional! (26 reviews)
Run down and kind of dirty...

"While your condo was beautiful, I did try to contact you the first night to let you know when we opened the sofa bed to use it for my 12 yo and it was covered by a GROSS egg crate that was in two pieces, littered with crumbs and food, and some mold. We quickly closed it up and she slept on the sofa ..."…"

Reviewed on Oct. 14, 2020

Grand Victorian, Luxury Condo, Top Floor Unit With Ocean Views, NO fees
The Sands Townhouses

The Sands Townhouses

3 out of 5
64 W Grand Ave, Old Orchard Beach, ME

Located in the heart of Old Orchard Beach, this condo building is within a 10-minute walk of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club ...

3.7/5Good! (25 reviews)

"Location is convenient because of the parking and beach being across the street. As far as cleanliness and noise it was horrible. Beds had hair and dirt in them. The train goes by twice a night that shakes the whole complex and is extremely loud. You can here everything through the walls. The neighbors ..."…"

Reviewed on Aug. 4, 2020

The Sands Townhouses
Free Beach Pass! New Cottage in 200 acre nature preserve, pool, minutes to beach

Free Beach Pass! New Cottage in 200 acre nature preserve, pool, minutes to beach

Kennebunkport, ME

Situated in Kennebunkport, this romantic cottage is 2.4 mi (3.8 km) from Arundel Barn Playhouse and 2.4 mi (3.9 km) from Seashore Trolley Museum. Brick Store ...

4.5/5Wonderful! (2 reviews)
Great vacation home in Maine

"We rented the house with our two children. Arundel was close to beaches and activities, but a 10-15 minute drive to Kennebunk and kennebunkport and ~20-30 minutes from Saco/Old Orchard Beach. The community is new, house and community amenities, including pool/terrain are beautiful and the owner easy ..."…"

Reviewed on Aug. 25, 2019

Free Beach Pass! New Cottage in 200 acre nature preserve, pool, minutes to beach
Coastal Cottage w/ Enclosed Front Porch, Pond View By Beach & Bike Path

Coastal Cottage w/ Enclosed Front Porch, Pond View By Beach & Bike Path

Old Orchard Beach, ME

Situated in Old Orchard Beach, this cottage is within 1 mi (2 km) of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club and Monkey Trunks Extreme ...

4.9/5Exceptional! (18 reviews)
On a Moose & Lobster Hunt

"We have wanted to go to Maine for sometime now! Love lobster, chowder, oysters and the one thing that was on our BUCKET LIST WAS to see a Moose! Checkmark done! We selected this quite, simple home for location and simplicity. We was very clean, comfortable, and easy to book and stay informed of my ..."…"

Reviewed on Oct. 30, 2020

Coastal Cottage w/ Enclosed Front Porch, Pond View By Beach & Bike Path
Nautical Point Maine-75 Yards to the Beach

Nautical Point Maine-75 Yards to the Beach

Old Orchard Beach, ME

Situated in Old Orchard Beach, this cottage is within 1 mi (2 km) of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club is 2.2 mi (3.6 km) away. ...

4.6/5Wonderful! (19 reviews)
Getaway

"Very relaxing. Enjoyed our visit. Close walk to the beach."…"

Reviewed on Oct. 27, 2020

Nautical Point Maine-75 Yards to the Beach
Historic-waterfront:'the Old River House'-in Town, on River

Historic-waterfront:'the Old River House'-in Town, on River

Kennebunkport, ME
The price is CA $1,259 per night from Jan 22 to Jan 23

Located in Kennebunkport, this beachfront vacation home is in the city center and within a 5-minute walk of Kennebunkport Village Green and W. Robert Paine Gallery. ...

4.9/5Exceptional! (54 reviews)
The place was wonderful and plenty room to spread out for our group.

"Excellent!"…"

Reviewed on Dec. 7, 2020

Historic-waterfront:'the Old River House'-in Town, on River
Nautical Point Maine - 75 Yards to the Beach

Nautical Point Maine - 75 Yards to the Beach

Old Orchard Beach, ME

Situated in Old Orchard Beach, this vacation home is within 1 mi (2 km) of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club is 2.2 mi (3.6 km) ...

4.5/5Wonderful! (15 reviews)
2020 stay

"Great location. Cute cottage. Hosts very nice. Thanks for all you did for our stay."…"

Reviewed on Oct. 12, 2020

Nautical Point Maine - 75 Yards to the Beach
2 min walk to the beach. Pet friendly condo

2 min walk to the beach. Pet friendly condo

Old Orchard Beach, ME
The price is CA $101 per night from Jan 19 to Jan 20

Situated on the waterfront, this condo building is within a 10-minute walk of Old Orchard Beach and Old Orchard Beach Pier. Dunegrass Golf Club and Ferry Beach ...

5/5Exceptional! (1 review)
Perfect location

"Perfect if you are looking for a place right on the beach! We didn’t use the house much besides sleeping/showering but it fit the description and had no issues. Would book again for another beach trip!"…"

Reviewed on Aug. 11, 2020

2 min walk to the beach. Pet friendly condo
Saco Old Orchard Beach KOA

Saco Old Orchard Beach KOA

3 out of 5
814 Portland Road, Saco, ME

Situated in Saco, this cabin is within 2 mi (3 km) of Funtown Splashtown USA, Monkey Trunks Extreme Aerial Adventure Park, and Aquaboggan Water Park. Saco Museum ...

Saco Old Orchard Beach KOA
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See all available properties in Portland
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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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Portland?
Yes, we give you a choice of vacation rentals in Portland close to Children’s Museum of Maine, or you can choose a more remote option if you’re looking for extra privacy while you relax. Tourists who visit Portland speak highly of the bustling port and array of shops. The great live music and acclaimed theater scene are some other things you might like to check out during your trip.
What are some of the best vacation rentals in Portland?
New Listing! Updated Getaway - Near Beach & Dining 2 Bedroom Home: Visitors like this Portland vacation home rental. It is located next to a golf course and has an outdoor tennis court, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a coffee maker. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Portland are Light-filled Studio Condo in the Center of Downtown-walk to Dining/shopping! and Historic-waterfront:’the Old River House’-in Town, on River.
How many vacation rentals are there in Portland?
Choose from 799 Expedia vacation rentals in Portland for a memorable vacation.
What can I see and do in Portland?
Children’s Museum of Maine and Portland Observatory are a couple of family-friendly sights, whereas cultural attractions include Maine Historical Society and Wadsworth-Longfellow House. You can also visit some other popular places in town, such as Cross Insurance Arena and Portland Head Light.
What are vacation rentals like in Portland?
Vacation rentals are privately owned properties you can reserve for several days or more in Portland. Vacation rentals feature extras such as kitchens and laundry facilities so you’ll have everything you want. If you’re concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You’ll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.

Other types of properties in Portland you may be interested in

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Free cancellationReserve now, pay when you stay
The price is CA $122 per night from Jan 31 to Feb 1
The Westin Portland Harborview
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street, Portland, ME
Free cancellationReserve now, pay when you stay
The price is CA $96 per night from Jan 19 to Jan 20
Embassy Suites by Hilton Portland Maine
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.