Holiday rentals in Portland Downtown

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Top-rated holiday rentals in Portland Downtown

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Top guest favourite
The entrance features a modern black exterior with a wooden door flanked by tall bamboo plants in round pots. A ladder leads up to a lofted area, while soft light is emitted from hanging lanterns inside. The patterned welcome mat adds a touch of style.
Tiny home in Richmond
5 out of 5 average rating, 156 reviews

Hawthorne Schoolhouse

Nestled between the popular and bustling streets of Hawthorne and Division in SE Portland, this tiny home provides a playful retreat. Walking distance to many shops, restaurants, bars, and cafes. Across from Sewallcrest Park and only a few blocks from Bagdad Theater and Powells Bookstore. Equipped with mini kitchen, lofted sleeping space, living room and bathroom. 80” 4K Smart Projector. Shared back yard with sauna. LGBTQA and 420 friendly. A golden retriever lives on property but please no pets

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, 232 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
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.

Guest favourite
A modern bathroom is featured with a deep soaking tub and sleek wood vanity. A round mirror and stylish light fixtures provide illumination. Neutral-toned tiles add warmth to the space, while a small plant decorates the bathtub area.
Home in Richmond
4.89 out of 5 average rating, 100 reviews

Hawthorne House - A+ Location! Pet Friendly!

Killer location!! An ez 2 min walk down the street from Hawthorne/Division in SE Portland! Enjoy the best restaurants, shops, bars PDX offers! Centrally located in great neighborhood! Main floor unit w/private access! Self check in! Bright and airy living spaces! Fully equipped kitchen for preparing delicious meals. Full sized wash/dryer. High speed Wi-Fi. Cozy bedroom w/plush queen-sized bed. Clean and modern bathroom stocked w/essentials. I'm excited to host you during your visit to PDX!!

Top guest favourite
A serene backyard oasis features a cascading water feature flowing over wooden planks and rocks. The modern tiny home with a dark exterior stands behind an elevated wooden deck, surrounded by lush greenery. Outdoor seating is visible, offering a calm retreat.
Guest house in Multnomah
4.95 out of 5 average rating, 132 reviews

Brand New Tiny Home/Pottery Studio in Cute Village

Welcome to DARK MODE, the tiny home/pottery studio 2 blocks from adorable Multnomah Village. Find peace in this serene hidden backyard oasis. Unit is 200 square feet plus loft and deck, behind the main house. Features include: - Jetted tub - Sleeping loft (queen) - Pull out bed (full) - Fire pit - Porch swing - Work desk - Cascading water feature - Outdoor dining table No kitchen but has a sink, fridge, microwave, water boiler, and plenty of wonderful food options within a few blocks.

Guest favourite
Flat in Pearl District
4.89 out of 5 average rating, 101 reviews

Luxurious king bed suite! Free Garage Parking

This high-end downtown apartment on the 6th floor offers breathtaking views of the city. The apartment is furnished with modern furniture and features a spacious living area with ample natural light. Equipped with underground parking, and access to nearby restaurants, entertainment venues, and shopping areas all within walking distance, this lofts prime location make this contemporary style apartment an ideal choice for those seeking a sophisticated and comfortable urban living experience.

Top guest favourite
A spacious sleeping area is featured, highlighted by a large wooden bed covered with white linens. Bright green walls offer a refreshing backdrop, while framed artwork adds interest. A small desk and chair are positioned beside the bed, with natural light streaming through a window.
Guest suite in Mt. Tabor
4.98 out of 5 average rating, 950 reviews

Sweet Hideaway in the trees, Mount Tabor

Sweet Hideaway is a little, cozy space for couples or solo travelers looking for a peaceful refuge in the trees, yet only a 10 minute drive to downtown. You will have your own entrance and enjoy a Tempurpedic queen bed, a smart TV, your private bathroom, a dining/kitchenette area with a bar table and stools, mini-fridge, microwave, toaster oven, coffee maker, tea, coffee, treats, utensils, a private table and chairs on the deck over the trees. For 2+ night stay, free use of washer/dryer.

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, 610 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.

Top guest favourite
Flat in Kerns
4.96 out of 5 average rating, 373 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
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, 259 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.

Top guest favourite
A spacious studio apartment features a cozy sleeping area with a wooden bed frame and soft bedding. A dining table with chairs is nearby, along with a comfortable sofa. Large windows allow natural light, and entertainment options include a flat-screen TV. Kitchen appliances are neatly arranged along one wall.
Guest house in Buckman
4.98 out of 5 average rating, 887 reviews

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, cable TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

Top guest favourite
A modern living area features a light gray sofa with decorative pillows, a sleek wooden coffee table, and a flat-screen television mounted on the wall. Large windows allow natural light to fill the space, offering views of the surrounding buildings.
Flat in Pearl District
4.96 out of 5 average rating, 139 reviews

Free Parking/Gym/Rooftop/Pearl District/Downtown

Akoya, one of the four types of Pearls in the world. Welcome to Pearl District in PDX! Simple yet elegant, the Akoya Stay combines convenience and style. Location is extremely walkable and offers quick access to Whole Foods and the MAX Light Rail. Simply step out of the building and get lost in the brewery blocks, fine dining, entertainment & premier retail shopping.

Popular amenities for Portland Downtown holiday rentals

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Avg. price$207 SGD$190 SGD$208 SGD$221 SGD$232 SGD$217 SGD$239 SGD$235 SGD$218 SGD$199 SGD$213 SGD$186 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 $51 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 McMenamins Crystal Ballroom

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