Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Top guest favourite

The living area showcases a light-filled space with polished concrete floors and a cedar tongue-and-groove ceiling. A comfortable sofa and coffee table are arranged on a colorful rug, while a flat-screen TV is positioned against a white wall. Large windows provide views of the outside greenery.

Guest suite in Richmond

4.97 out of 5 average rating, 409 reviews

Walk to Se Division from a Sleek, Architect Designed Space

My wife, Raechel, and I originally designed and built this ADU ( accessory dwelling unit ) with the intention of living there full time, but due to a change of plans, it's available to you. The space was designed by Buckenmeyer Architecture, and was constructed by me. Our space features many unique elements such as: paper-composite counter tops and bathroom tiles, real copper backsplash and bathroom walls, polished concrete floors, cedar tongue and groove ceiling, burnt cedar siding, 16' multi-slide window wall (please open and close slowly), moveable cedar slat screens, custom frosted glass pocket doors, and custom apple-ply kitchen cabinets by George Ramos We love to cook and put great effort into getting the kitchen space dialed in. The kitchen features: bosch speed oven (microwave and convection oven), bosch dishwasher, 2 burner gas range, and Pull-out exhaust and lighting We hope you enjoy the space and neighborhood as much as we do! The guesthouse has it's own separate entrance with a smart lock for convenient self check in. You'll receive the unique code prior to check in. We live in the main house and are available to help make your stay as great as possible. We value your privacy and will not stop by unless contacted. Please text for the quickest response. Nearby Division Steet is known as restaurant row and features some of the best food in Portland, including Pok Pok, Salt and Straw, and Ava Genes. On a warm summer night, there will be hundreds of people just going for a stroll up and down Division. Our guesthouse is a 2 minute walk from a major bus stop, and a Biketown stall where you can rent a bike by the trip. There is no dedicated parking space but there is an abundant amount of non-metered unlimited on-street parking directly in front of our guest house on 28th pl. The Roku Tv enables you to login to your entertainment provider of choice, please remember to logout. The Bose Soundbar is wired to output the TV's audio, but can also be connected to via bluetooth by hitting the bluetooth icon on the Bose remote and pairing with your device. We provide locally roasted coffee beans, a manual conical burr grinder, insulated french press, stovetop kettle, and creamer + sugar. Please enjoy the in-shell Hazelnuts!

Guest favourite

A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.

Home in Multnomah

4.96 out of 5 average rating, 122 reviews

Portland Modern

Welcome to our Midcentury Modern – a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this completely renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. This house is perfect for friend groups, families or corporate retreats. Note: 4 bedroom, 2 bath, 2 kitchen.

Top guest favourite

A shaded patio area is featured, showcasing a set of three wicker chairs with cushions positioned around a small table. A pergola covered in vines provides natural cover, while a landscaped yard and colorful garden shed are visible in the background.

Guest house in Woodstock

4.98 out of 5 average rating, 818 reviews

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

Guest favourite

The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.

Guest house in Piedmont

4.98 out of 5 average rating, 217 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Guest favourite

A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.

Guest house in Clackamas

4.97 out of 5 average rating, 209 reviews

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Top guest favourite

The exterior of the home is highlighted by contemporary design elements and a clean white facade. A flowering tree adds a touch of color, while large glass doors invite natural light into the living area. Surrounding landscaping is thoughtfully arranged with minimalistic plantings.

Guest house in Arbor Lodge

4.99 out of 5 average rating, 525 reviews

Accessible, AIA-Award Winning, Urban Garden Oasis

A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

Top guest favourite

A panoramic view of snow-capped Mt. Hood is framed by open double doors, providing a striking backdrop to the interior. The rustic dining area features wooden chairs and a table, while the floor is set with dark tiles that contrast with the scenic landscape outside.

Flat in Sandy

4.99 out of 5 average rating, 405 reviews

Gorgeous Mt. Hood View, Ski, Hike or Mt.Bike

Welcome to Sandy Oregon, the Gateway to Mount Hood. This Luxurious cabin-feel home, custom built by top notch craftsman and designer, features breathtaking panoramic views of Mt. Hood and the Sandy River. The view is rated one of the best in the Northwest. Enjoy a glass of wine while sitting by the outdoor fire pit, take a short drive to Timberline Lodge for skiing or snowmobiling, go hiking in the Mt. Hood forest or Mountain Biking at world class "Sandy Ridge". Your options are unlimited!

Guest favourite

An open studio layout is highlighted by an inviting soaking tub surrounded by plants. Light-colored walls enhance the airy feel, while warm wooden elements, like a platform bed and cabinetry, provide a harmonious balance. A cozy seating area and kitchen are subtly integrated.

Guest suite in Woodlawn

4.97 out of 5 average rating, 603 reviews

The Sneakaway

Built to feel like a little touch of luxury, with the quaintness and quality of a craft home. This place is a true sneak-away with a two person soaking tub, marble shower, king tempurpedic bed and a fully stocked kitchen. This open studio has 15 ft ceilings allowing ample sunlight and a large, light feeling. This house was designed and built by me my friends so no detail is overlooked or unintentional. This was our labor of love for a year and Im so excited to now be able to share it.

Guest favourite

An architectural micro home is nestled among lush greenery, surrounded by trees. A wooden exterior enhances the natural setting. The structure features a small side porch and multiple large windows, allowing light to flood the interior. A pathway made of stones leads to the entrance.

Guest house in Eliot

4.83 out of 5 average rating, 156 reviews

The Haseman House

Come stay in our Architectural micro home in NE Portland. Close to Mississippi and everything that NE Williams has to offer. Thoughtfully deigned with many amenities. A great WFH vacation retreat. This little house is located in the back of a main house. The backyard is shared with the main front house. There is only street parking but it is free and typically available. We are close to public transportation and rental bikes as well as an organic grocery store... very walkable.

Top guest favourite

The guest home is set behind a picturesque entrance adorned with an elegant gate and carefully arranged greenery. Paved stone pathways guide visitors through the lush surroundings, leading to the welcoming facade of the home, seamlessly integrated with the tranquil, tree-lined environment.

Guest suite in Portland

5 out of 5 average rating, 527 reviews

IndigoBirch: Luxurious Zen Garden Retreat: Hot Tub

Look no further- as a member of The IndigoBirch Collection™️, our guest home stands as a top-tier experience on Airbnb. Located two blocks away from Reed College, IndigoBirch is nestled on a quiet tree-lined street in the highly desired & historic neighborhood of Eastmoreland. Our location is perfect for the adventurer looking to explore Portland. The guesthouse is two blocks away from public transportation, 12 minute drive to downtown Portland, and 20 minutes to PDX Airport.

Top guest favourite

The entrance to the guesthouse features a warm wooden door framed by lush greenery. Potted plants and a natural wood stool create an inviting atmosphere. Soft string lights hang above, enhancing the serene outdoor space surrounded by trees.

Guest house in Woodlawn

4.99 out of 5 average rating, 265 reviews

Sorta Summer House w/ sauna & outdoor shower

The guesthouse is a private oasis in the city. It's surrounded by fruit trees and tall Chinese Mountain bamboo. It's a quick walk to Woodlawn Park, great coffee, a bakery, pizza, whiskey bar, a brewery, seasonal farmers market, and minutes from Alberta Arts District. The airy, open floor plan is filled with natural light, mixed textiles and warm woods. A cedar-surround outdoor shower and private 5x7 Finnish sauna lend to the spa-like setting. Guests say it’s hard to leave!

Top guest favourite

Flat in Kerns

4.96 out of 5 average rating, 356 reviews

Studio in Walkable Foodie Heaven

We're on a quiet side street – right around the corner from a dynamic restaurant scene in Kerns, the 5th coolest neighborhood in the world. Stroll to parks, live music, vintage shops, and a vintage movie theater. Walk, Lyft/Uber, bicycle, or use Portland’s amazing public transportation everywhere. Tall windows overlook greenery and a cozy porch. Our family's 1900 house has been divided into separate apartments. Its like an artsy hotel room, but much more homey!