Portland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Portland

The Weldon Hotel
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (80)
"Absolutely beautiful place to stay. "
The price is ￥43,465
￥58,448 total
includes taxes & fees
Oct 1 - Oct 2
The Weldon Hotel
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very smooth and easy check-in. Very nice room and bathroom. Thank you so much for letting us stay! "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is ￥15,499
￥26,580 total
includes taxes & fees
Sep 29 - Sep 30
Private Entrance Residential Portland
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (62)
"We stayed for a group trip to Portland and this was the perfect spot. Location is fantastic, lots of comfortable sleeping options, and great communication from the host. Highly recommend! "
The price is ￥106,279
￥160,734 total
includes taxes & fees
Sep 29 - Sep 30
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
The price is ￥13,949
￥24,708 total
includes taxes & fees
Oct 22 - Oct 23
Studio Unit Walkable Everywhere
Spacious Historic Home | 7BR West End for Groups
Marina

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (6)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
The price is ￥103,622
￥236,788 total
includes taxes & fees
Sep 25 - Sep 26
Spacious Historic Home | 7BR West End for Groups
The Cottages at Cabot Cove
Tranquility Cottage Queen Bed Garden View | Living area | 24-inch Smart TV with cable/satellite channels, TV, DVD player

The Cottages at Cabot Cove

3.5 star property
9.6 out of 10, Exceptional, (39)
"Beautiful, charming and staff was excellent "
The price is ￥69,276
￥83,412 total
includes taxes & fees
Sep 25 - Sep 26
The Cottages at Cabot Cove
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Outdoor dining

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (63)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
The price is ￥117,940
￥220,426 total
includes taxes & fees
Sep 29 - Sep 30
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
68 East Grand Ave
Luxury Condo | Private kitchen | Full-size fridge, microwave, oven, stovetop

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave
Bright and airy condo with beachfront access and walkable entertainment nearby
Fridge, microwave, oven, stovetop

Bright and airy condo with beachfront access and walkable entertainment nearby

6.8 out of 10, (3)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby
Beach House ∆ Prime Location ∆ Steps to the Ocean
Beach nearby, sun loungers, beach towels

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (48)
"We loved everything about our stay here. Perfect location right on Old Orchard Beach. The house is perfect for what we needed/wanted. Wish we could have stayed longer. We would definitely come back for a longer stay next time we’re in Maine. "
The price is ￥22,164
￥73,070 total
includes taxes & fees
Sep 25 - Sep 26
Beach House ∆ Prime Location ∆ Steps to the Ocean
Cozy Coastal Condo with Parking – Walk to Beach & Town
Beach nearby

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.6 out of 10, Excellent, (13)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (228)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Grand Victorian on the Beach, Summer
Fridge, microwave, oven, stovetop

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (78)
"I would recommend this place to everyone. We had a great time."
Grand Victorian on the Beach, Summer
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Beach

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

9.8 out of 10, Exceptional, (45)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Full sized home
Terrace/patio

Full sized home

9.8 out of 10, Exceptional, (42)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is ￥29,522
￥53,739 total
includes taxes & fees
Oct 15 - Oct 16
Full sized home
350 Yards to the beach. Pet friendly!
Beach

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very Good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
350 Yards to the beach. Pet friendly!
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
Gorgeous ocean-front home with stunning beach views
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (219)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
The price is ￥25,832
￥50,199 total
includes taxes & fees
Oct 25 - Oct 26
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Historic Kennebunkport home only 0.3 miles to Dock Square
Marina

Historic Kennebunkport home only 0.3 miles to Dock Square

10.0 out of 10, Exceptional, (73)
"Wonderful home close to downtown. Comfortable house and great host!"
The price is ￥39,855
￥85,435 total
includes taxes & fees
Sep 29 - Sep 30
Historic Kennebunkport home only 0.3 miles to Dock Square
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 Portland Hotel Reviews

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent
"Clean, staff very helpful and courteous, convenient location."
Christopher 5-night trip
Posted 7 hours ago
Cambria Hotel Portland Downtown-Old Port

Find out more about Portland

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
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Look no further and take a look at our great range of rental properties in Portland!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Portland?

Yes, we give you a choice of vacation rentals in Portland close to Bayside Bowl, 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 entertainment choices and great live music are some other things you might like to check out during your trip.

What are some of the best vacation rentals in Portland?

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.: Visitors like this Portland vacation home rental. It is located on the beach and offers a fireplace, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

How many vacation rentals are there in Portland?

Choose from 84 Expedia vacation rentals in Portland for a memorable vacation.

What can I see and do in Portland?

Bayside Bowl and Portland Observatory are a couple of family-friendly sights, whereas cultural attractions include Merrill Auditorium and Portland Museum of Art. While here, Fore Street Gallery and Casco Bay Lines Ferry Terminal are other places worth a visit.

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.