
Holiday rentals in Portland
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Top-rated holiday rentals in Portland
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Other great holiday rentals in Portland
Superhost

Home in Bridgton
5 out of 5 average rating, 105 reviewsWren Cabin + Wood fired Sauna
AmyRating, 5 stars2 days ago
Great spot for a private getaway! Hosts were very friendly, flexible and ensured we had everything we needed. Would absolutely visit again and recommend 100%
Superhost

Flat in Downtown Portland
4.88 out of 5 average rating, 234 reviewsLovely studio in downtown Portland
DoreenRating, 5 stars2 weeks ago
First time in Portland and this apartment was perfect for two people. Comfortable bed, clean kitchen. We did not have a car and did not need one to get around downtown. Literally five minutes to the harbor and so many great restaurants. Would absolutely stay there again.
Superhost

Flat in East End
4.98 out of 5 average rating, 153 reviewsModern Luxury with Bay Views * 5 Star Location!
MichaelRating, 5 stars2 days ago
The apartment and its furnishings exceeded our expectations. High quality amenities and a nice welcome gift from the host was a treat - as were the Holy Donuts the next morning! Easy walk into Old Port and the wharfs, sidewalk shops and restaurants. And don’t forget to enjoy the Adirondack chairs on the new terrace overlooking the park below.
Superhost

Treehouse in Pownal
4.98 out of 5 average rating, 106 reviewsThe Copper Fox Treehouse
JanRating, 5 stars5 days ago
This was my second visit to the Fox and won’t be my last! The setting is snugly tucked back in the woods on the property with hosts nearby enough to be comforting but with privacy to enjoy the quiet. We hiked the trails around Bradbury Mountain that back right up to the property and made a few small jaunts into Freeport and up along the MidCoast area. Heidi and Nicolas have built and curated a beautiful spot with plenty of off-grid activities and games in the treehouse (love the no-TV feature) and the amenities are plentiful and in great condition. The binder with local restaurants and attractions is wonderfully helpful! Even though we are from the area, we found several things listed we’d love to visit in the future. I cannot recommend the Copper Fox enough! It’s a great place to book and genuinely feel life the way it should be in Maine.
Superhost

Guest house in Portland
4.96 out of 5 average rating, 320 reviewsBeautiful large studio on the ocean.
MarkRating, 5 stars1 week ago
We really enjoyed our stay at Hilary’s place. It was clean and was in a perfect location, quiet and on the water yet minutes from the Old Port and rest of the city. Hilary was a great host and checked in to make sure we had everything we needed.
Superhost

Cabin in Georgetown
4.99 out of 5 average rating, 137 reviewsSauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C
CraigRating, 5 stars1 day ago
Excellent place to stay in a beautiful part of Maine, hope to get back here!
Superhost

Tiny home in Portland
4.96 out of 5 average rating, 481 reviewsThe Garden Cabin Tiny Home
JuliaRating, 5 stars1 week ago
We loved staying at Jennifer and Darcys! We could have moved right in. They have created such a tranquil environment, and you can tell they pour their heart into the space! Even though you are staying behind their house, it is quite private back there, and you are separated by their amazing vegetable garden. They've really thought of every little detail both inside and out. And the bathroom smelled great! Don't think twice!
Superhost

Flat in West End
4.84 out of 5 average rating, 866 reviewsSelf-check-in | Parking | Washer + dryer | Desk |3
MasonRating, 5 stars1 week ago
Beautifully decorated apartment with an amazing atmosphere from both the room and the surrounding area that made the trip. Everything you could need for a perfect short or long stay is provided. Would highly recommend for anyone wanting to experience a surreal stay Portland.
Quick stats about holiday rentals in Portland
Total rentals
1.6K properties
Total number of reviews
172K reviews
Family-friendly rentals
850 properties are a good fit for families
Pet-friendly rentals
450 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
800 properties have a dedicated workspace
Destinations to explore
- Private suite rentals Portland
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Wentworth by the Sea Country Club
- East End Beach
- Cliff House Beach
- Brunswick Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Funtown Splashtown USA
- Ferry Beach
- Cranmore Mountain Resort
- Purity Spring Resort
- King Pine Ski Area
- Crescent Beach
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