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Holiday rentals in Portland

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Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Private room
  2. Portland
Spacious, Private Bedroom- Close to Everything!

Minimum 30 Day Stay 250+ square feet of private bedroom space! Great location- close to interstate, downtown, Back Cove, USM and local bars and restaurants. Great place to stay for grad students, travel nurses or other transient professionals! -Bedroom has Pin Pad lock for address safety and privacy -Laundry in building

  1. Entire rental unit
  2. Downtown Portland
Third-floor condo steps from dining & Old Port with balcony, AC, harbor view

 

  1. Entire apartment
  2. East End
Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!

 

Holiday rentals for every style

Get the amount of space that is right for you.

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  • Unique stays

Stay near Portland's top sights

Photo of Peaks Island
Peaks Island116 locals recommend
Photo of Fort Williams Park
Fort Williams Park108 locals recommend
Photo of Portland Head Light
Portland Head Light120 locals recommend
Photo of Portland Museum of Art
Portland Museum of Art170 locals recommend
Photo of Bug Light Park
Bug Light Park59 locals recommend
Photo of Casco Bay Lines
Casco Bay Lines54 locals recommend

Other great holiday rentals in Portland

SUPERHOST
  1. Entire rental unit
  2. East End
East End, Walk to the Old Port, with Parking
  1. Entire rental unit
  2. Portland
Comfortable two bedroom Apartment
SUPERHOST
  1. Entire rental unit
  2. East End
Modern East End studio, perfect Portland home base
SUPERHOST
  1. Entire rental unit
  2. East End
East End - MunjoyHill - Just Steps from Everything
SUPERHOST
  1. Entire rental unit
  2. Arts District
Modern Studio Loft w/ Parking in Perfect Location
SUPERHOST
  1. Entire rental unit
  2. East End
Cozy Studio on Munjoy Hill (Lic.#STHR-000186-2018)
SUPERHOST
  1. Entire rental unit
  2. West End
Location, location!
SUPERHOST
  1. Entire guest house
  2. Portland
The Carriage House at Libbytown
  1. Entire rental unit
  2. West End
Stunning - modern 2 bedroom Victorian mansion pad
SUPERHOST
  1. Entire rental unit
  2. East End
Cozy + Walkable • East End Getaway
  1. Entire loft
  2. Portland
Lily's Loft; Charming one bedroom studio
SUPERHOST
  1. Entire rental unit
  2. East End
RETRO BnB in the Heart of East End Portland
  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland