Search Vacation Homes in Portland

  • Plan, book, stay with confidence

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

Compare 71 Vacation Homes in Portland with updated reviews, rates, and availability.

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

8.8 out of 10, Excellent, (15)
"Convenient to walking to town , great restaurants in the area for breakfast & dinner, house was perfect, comfortable, well maintained great off street parking and had everything we could ever had needed."
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!

NEW LISTING! Prime City Living Townhouse by RedAwning

2.0 star property
8.0 out of 10, Very Good, (1)
"It was very convenient. "
The price is AED 745
AED 2,038 total
includes taxes & fees
12 Jan - 13 January 2025
NEW LISTING! Prime City Living Townhouse by RedAwning

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House

Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade

9.0 out of 10, Wonderful, (18)
"Great location! Be prepared to climb a couple of flights of stairs, but then you are all alone. Private little deck is nice. Hot water in the kitchen sink, but not any in the shower or bathroom sink so we were able to get clean, but not conveniently. Also couldn't get the living room TV to work. We were too busy exploring the town though."
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade

The best place for the money!!!

8.6 out of 10, Excellent, (19)
"We had a good stay here for a week. It's a cool property but a bit run down. The couch is very dirty and stained. We had issues with the AC while we were there. One of the light fixtures was falling out of the ceiling, and the fire alarms were hanging open without any batteries. The beds were decent but quite loud when you move. The one shower in the property leaked water all over the floor and required extensive clean up every time it was used. The property manager was very responsive and...
The best place for the money!!!

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (23)
"The place was beautiful and spotless. Spacious shower and bath. It and very confortable. Fantastic restaurants within walking distance. The off street parking was a huge bonus."
The price is AED 687
AED 1,353 total
includes taxes & fees
1 Jan - 2 January 2025
Modern & Sunny House Steps from the Promenade. Private Parking!

Beautiful, single story ranch. Next to city park with ocean view!

8.4 out of 10, Very Good, (7)
"Conveniently located property, responsive hosts. A few maintenance issues with the property but we enjoyed our stay. "
The price is AED 2,571
AED 4,116 total
includes taxes & fees
6 Jan - 7 January 2025
Beautiful, single story ranch. Next to city park with ocean view!

"Glamp" out near downtown Portland w/outdoor patio, fire pit & outdoor shower!

9.2 out of 10, Wonderful, (9)
"This was a great spot to stay for a guys weekend. Location is a short drive to Old Port where we spent most of our time. When we weren't out and about the backyard with a fire pit and corn hole boards was perfect for hanging out. Ryan was great and responsive."
"Glamp" out near downtown Portland w/outdoor patio, fire pit & outdoor shower!

Gardensong Retreat - Luxury, Nature & Space

Gardensong Retreat - Luxury, Nature & Space

Luxurious Penthouse with Modern Design in Downtown

9.2 out of 10, Wonderful, (5)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

Entire Historic Home - Portland West End

10.0 out of 10, Exceptional, (1)
Entire Historic Home - Portland West End

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (57)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is AED 599
AED 1,550 total
includes taxes & fees
26 Dec - 27 Dec
Elegant condo - walk to Portland's best restaurants & Old Port

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (24)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (55)
"The property is an older triplex, interior is nice. Neighborhood is quiet. Close to historic wharf area. Easy to walk to local restaurants and sites. I had my dog with me and appreciated the back yard. Of note, there is no washer/dryer in the unit. No dishwasher, but this wasn't a problem. Parking is limited to on-street and would be an issue if more than one car required space. The only bathroom and both bedrooms are on the second floor and might be a consideration for anyone with mobility...
The price is AED 396
AED 956 total
includes taxes & fees
5 Jan - 6 January 2025
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (21)
"The reclining furniture was our favorite after running around all day! Very comfortable beds! Great place to stay!"
The price is AED 999
AED 2,574 total
includes taxes & fees
23 Dec - 24 Dec
Convenient Portland home 3 miles from Downtown

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

10.0 out of 10, Exceptional, (135)
"Wonderful host, beautiful apartment, and great location. "
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

Cozy Historic Home on Great Diamond Island

5.0 out of 10, (2)
"We arrived by ferry on cold and very rainy Monday night. We were apparently unexpected, and the house wasn't ready. Staff at the Inn picked us up at the ferry, and dropped us at the Inn while they checked the property. They brought sheets to make the bed, which wasn't made. The house was musty and dirty, the bathroom had not been cleaned, floors had not been mopped, blankets and dish towels were musty and unusable, there were no potholders, and dishes were left in the dish drainer from previous...
Cozy Historic Home on Great Diamond Island
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.
Don't see what you're looking for?
See all available properties in Portland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Portland

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (24)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (142)
"We had a wonderful night in Portland! We spent the afternoon shopping in Freeport and arrived at the apartment around 5. Very easy finding parking on the street and no trouble getting inside. The apartment is absolutely adorable! Between the colors and decorations, it just gives off this girly, cozy vibe. There were 4 of us and we all had room to sleep comfortably. Wish we could have stayed another night! "
The price is AED 466
AED 945 total
includes taxes & fees
1 Jan - 2 January 2025
Glorious getaway on Portland's Eastern Promenade.
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.