Holiday rentals in Portland Downtown

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Top-rated holiday rentals in Portland Downtown

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Top guest favourite
A modern living space features a teal sectional sofa adorned with vibrant throw pillows. A glass coffee table rests atop a textured rug, and the kitchen showcases wooden cabinetry and stainless steel appliances, with natural light enhancing the atmosphere.
Home in Ladd's Addition
5 out of 5 average rating, 229 reviews

New Home Near it All on Division w/ EV Charger

Welcome to The Eloise — a bright, art-filled home centrally-located in the bustling Division/Clinton district of SE Portland. This beautiful ADU has it all. A suite with king bed & bathroom with a luxurious shower; workspace w/ speedy wi-fi; lounge; two TVs a full kitchen, & EV charger. Premium amenities & local treats await you. Tucked into a quiet street just off Division, you’re within walking distance to restaurants, shops, bars, venues, bus & TriMet lines & a 5-minute drive to Downtown.

Top guest favourite
A detached studio features a charming A-frame design, surrounded by lush greenery. A stone patio with outdoor seating complements the inviting entrance, where large windows allow natural light to fill the space. The setting provides a serene atmosphere, ideal for relaxation.
Guest house in Westmoreland
4.98 out of 5 average rating, 660 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, newly constructed detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

Top 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, 229 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.

Top guest favourite
A bright living space is highlighted by sloped ceilings and skylights. A comfortable sofa and armchair are arranged near a coffee table, with a dining area featuring white chairs in the background. The kitchen is partially visible, enhancing the open layout.
Flat in Portland
4.94 out of 5 average rating, 136 reviews

Spacious 1BR+ by NW 23d. Free parking & cleaning!

If you're looking for a great value and a convenient location (no car needed!), you have found the place! Steps away from NW 23rd St, this is a spacious 700 sq. ft., 1 BD/1BA private apartment. PLENTY of room to play with fido, cook, hang out, work, etc. Free street parking, your own outdoor balcony, fast wifi, plus easy access to all things shopping and food. Whether it's your first or fiftieth visit to Portland, this apartment has all you and your family/friends need for a comfortable 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, 536 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 modern studio space is showcased with a vibrant orange sofa and a sleek blue chair. Reflected in the large mirrors, natural light enhances the room's ambiance. A dining area with stylish seating is visible in the background, alongside neutral-toned flooring and cozy rugs.
Flat in Overlook
4.95 out of 5 average rating, 606 reviews

Close-in, private Overlook retreat.

The Overlook neighborhood is one of Portland's hidden gems. Quiet, tree lined, yet only a few minutes from all the action Portland serves up. Walk or ride to meals, brewpubs or shopping in the Mississippi and Williams districts. Hop a train (three blocks away) to all quarters. Or, to unwind, walk to Overlook or Mocks Crest parks for sweeping views of downtown Portland, Forest Park and the Willamette River. Please read on to see if the studio's lower ceiling is the right fit for you.

Guest favourite
A modern living space features a comfortable gray sofa adorned with patterned throw pillows. Two tables in varying heights are placed in front. A large window allows natural light in, and a nearby plant adds a touch of greenery. Laundry appliances are accessible through a door.
Home in King
4.92 out of 5 average rating, 188 reviews

Modern Apt | Close to Everything

Located within the trendy Boise neighborhood and only minutes to central Portland is this chic sun-filled apartment that offers all the modern comforts of home. With stylish décor and bright open plan living, the apartment features a fully equipped kitchen, soft comfortable furnishings, a spacious master bedroom and a sparkling modern bathroom. Walk to the popular Williams and Mississippi streets with its top restaurants, coffee shops and Portland’s world-famous food carts.

Top guest favourite
Flat in Kerns
4.96 out of 5 average rating, 371 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!

Top guest favourite
A warm sleeping area features a spacious bed framed by two wooden nightstands with lamps. A bright yellow throw blanket lays across the bed. The walls are painted a deep teal, and natural light enters through a window with a beige shade. A decorative piece on the wall adds character.
Guest house in Sullivan's Gulch
5 out of 5 average rating, 448 reviews

Cozy, Stylish Bungalow w/ Fireplace & Full Kitchen

Enjoy a comfy retreat in this cozy and bright studio with a private bathroom, air conditioning, fireplace, full kitchen and work desk. Conveniently located within walking distance to local restaurants, coffee shops, retail stores, and parks. Centrally located in Portland and just 3 miles from downtown. Take a stroll through Historic Irvington and enjoy some of the most beautiful homes and old growth trees that Portland has to offer.

Top guest favourite
The cottage exterior is showcased with a warm red facade and a welcoming entrance featuring a glass-paneled front door. A private patio with wooden doors opens to the yard, which is surrounded by fencing and landscaped with mulch and plants.
Guest house in Overlook
4.96 out of 5 average rating, 258 reviews

Private guesthouse w/ yard, firepit, patio, loft

We built this cottage in 2019 using many reclaimed materials, and we hope you love it as much as we do. Located just one block from all the best North Portland has to offer; coffee shops, brunch spots, neighborhood bars and shops. Very easy access to public transit (light rail and bus) and only one exit from downtown. 15 minutes to the airport and 8 minutes to Forest Park. Includes a spacious private yard/patio and firepit.

Guest favourite
A bright studio space is depicted with warm wooden walls and ceilings. A spacious bed with white bedding is positioned in the foreground, while a small kitchenette with wooden cabinetry is visible in the background. Natural light enters through a door leading to an outdoor area.
Guest suite in Cully
4.96 out of 5 average rating, 521 reviews

Cozy Studio In NE PDX (Cully/Beaumont-Wilshire)

Cozy (240 sq ft), private studio space located in NE Portland on the edge of the Cully and Beaumont-Wilshire neighborhoods. We are located on a bike route and about a 12-minute walk to NE Fremont Street (many restaurants, coffee shops, bars), 12 min by car to the airport, and 15 min to downtown. Small kitchenette with microwave, mini-fridge, toaster oven, and coffee/tea supplies. Queen bed, super comfy mattress.

Top guest favourite
An orange sofa is positioned in the center of a well-lit room with hard tile flooring. Framed art pieces are displayed on the wall above the sofa. A round, knitted pouf adds a cozy touch in front of a soft area rug. A doorway leads to a bathroom area.
Guest suite in Goose Hollow
4.93 out of 5 average rating, 106 reviews

Garden hideaway steps from classic PDX favorites

Tucked away in a secret community of old Portland classic homes, we are perfectly situated for your visit to the Rose Garden, Japanese Garden, Providence Park, shopping on 23rd street or imbibing on 21st street. We are a are a nice walk from the culinary delights of the Pearl District and 7 minutes afoot from the Goose Hollow light rail stop.

Popular amenities for Portland Downtown holiday rentals

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Avg. price$207 SGD$191 SGD$209 SGD$222 SGD$233 SGD$218 SGD$240 SGD$236 SGD$219 SGD$200 SGD$214 SGD$187 SGD
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Quick stats about holiday rentals in Portland Downtown

  • Total holiday rentals

    Explore 260 holiday rentals in Portland Downtown

  • Nightly prices starting at

    Portland Downtown holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,750 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    260 of Portland Downtown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Portland Downtown rentals

  • 4.7 Average rating

    Portland Downtown stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Portland Downtown’s top spots include Powell's City of Books, Tom McCall Waterfront Park and Arlene Schnitzer Concert Hall

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