Holiday houses in Portland Downtown

4.91 out of 5 average rating, 156 reviews

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 Portland

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!!

Guest suite in Southwest Portland

A spacious deck features a round table surrounded by four chairs. The view captures a vibrant sunset over the Portland skyline, with a blend of city buildings and natural greenery in the foreground. The sky displays hues of orange, pink, and gray.

Magnificent finishes and views!

A rare opportunity to get to stay in Portland's most coveted view neighborhood, full of multi-million dollar homes, and under 200 feet away from the house with the highest listing price in Portland (at $7mil). This is an every surface touched renovation in 2023/2024, utilizing Italian tile, Oregon black walnut, rare mid-century modern furniture pieces and decades old original works of art. We renovated this space in the vision of the finest boutique hotels we have stayed at throughout Europe.

4.98 out of 5 average rating, 56 reviews

Apartment in Portland Downtown

A well-lit living area is viewed through an open doorway, showcasing large floor-to-ceiling windows that reveal lush green hills and vibrant cityscapes. A cozy seating arrangement, including a light-colored chair and dark ottoman, complements the inviting atmosphere of the space.

Luxury Living in Prime Location FREE Airport Rides

FREE AIRPORT [pickups/drop offs] get personally picked up, no wait on Lyft or Uber. Incredible city views! Centrally located studio. Walk straight to world famous Powells Bookstore on the iconic Burnside Street! Or simply enjoy southwest hills sunsets from the comfort of your living room with floor to ceiling windows! Portland Street Car station is located across the street, a block from WholeFoods Markets! Lots of iconic clubs, bars, restaurants, and entertainment within walking distance.

4.94 out of 5 average rating, 18 reviews

Apartment in Northwest Portland

Historic 2BR | Walk to NW 23rd Shops & Eats

✨ Charming Northwest Portland Flat in Alphabet District ✨ 🏙️ Heart of NW 23rd — walk to top shops & cafes 🛏️ 2 cozy bedrooms, sleeps 4 guests comfortably 🍳 Full kitchen with coffee maker & wine glasses 🛋️ Smart TV & fast WiFi throughout 💻 Laptop-friendly workspace for remote work 🌿 Private entrance & porch for your morning coffee ❄️ AC & heating for year-round comfort 🔒 Entire apartment — no shared spaces 🍽️ Steps from NW 23rd's best dining & shopping. Free street parking.

4.76 out of 5 average rating, 191 reviews

Home in Southwest Portland

A panoramic view of the city skyline is captured during sunset, showcasing vibrant orange and pink hues in the sky. Modern buildings stand prominently against the colorful backdrop, with trees framing the scene in the foreground.

Urban Oasis with Spectacular Views

The downtown and mountain views are a showstopper! Peaceful and centrally located place with many amenities and an easy walk to downtown. Stylish and charming studio apartment attached to the home where the host lives. It has its own private entrance and balcony. This apartment is perfect for the business traveler, longer-term stays, artist's retreat or a weekend urban get-away. Super close to downtown, PSU, OHSU, shopping and tourist destinations. Easy on and off the highway too.

4.87 out of 5 average rating, 71 reviews

Apartment in Northwest Portland

Upscale NW Portland Lofts - Modern, Walkable

✨ Bright NW Portland Loft Near 23rd Ave ✨ 🏙️ Soaring ceilings & modern design touches 🛏️ 2 bedrooms, sleeps 4 comfortably 🍳 Full kitchen with coffee, blender & wine glasses 🛋️ Dining table, TV & fast WiFi 💻 Laptop-friendly workspace for remote work 🌬️ AC, ceiling fans & room-darkening shades 🔒 Private entrance — entire place is yours 🧺 In-unit washer & dryer for extended stays 🍽️ Heart of NW 23rd dining & shopping. Paid parking nearby.

5.0 out of 5 average rating, 48 reviews

4.99 out of 5 average rating, 478 reviews

An open living space features a stylish wooden staircase, enhancing the flow of natural light. A modern dining table is accompanied by Arne Jacobsen Ant dining chairs. Decorative plants and a round mirror add a touch of elegance, while large glass doors provide a view of the outdoor area.

Home in Portland

Modern Guesthouse in Portland's Central Eastside

Tall ceilings, an open staircase and walls of windows flood the space with light (even in Portland), while molded plywood Eames chairs add mid-century style. Located in the heart of Portland within walking distance to great restaurants, coffee and parks. Fast, gigabit fiber internet, full kitchen, large table, and private outdoor spaces help maximize your stay and comfort, whether you're alone or with a group. Editor's pick in Dwell.

Home in Northwest Portland

A three-story home is depicted with a distinctive dark exterior and a peaked roof. The entrance is framed by a landscaped area featuring bushes and steps leading to the front door. A garage is visible beneath the living space, and a fence encloses the property.

Old Portland Charmer

Nestled in one of Portland's most desirable neighborhoods, this charming home beautifully combines the character of the early 1900s with modern style and amenities. Walk to some of Portland's best restaurants, shops, and attractions just a short walk away. The completely remodeled home features a spacious backyard, abundant natural light, and the added convenience of off-street parking— simple luxuries that make all the difference.

4.99 out of 5 average rating, 71 reviews

4.96 out of 5 average rating, 265 reviews

Home in Portland

Holiday Home

Greetings Welcome to Portland! We hope that you will have a wonderful time in our beautiful city and that you will enjoy your stay here at Oasis in PDX We love entertaining and have put thought into creating different seat groupings, both inside and out, that invite people to relax both near to and apart from the main living areas, so that one-on-one conversations can take place without others in the group feeling excluded.

Home in Southwest Portland

An airy dining area is illuminated by natural light from large windows, showcasing views of the surrounding landscape. A modern table with chairs is positioned near the window, while stylish bar stools line the kitchen counter, offering a subtle separation between spaces.

Serene Forest Retreat mins to Downtown

Escape to one of Portland's most peaceful neighborhoods in this bright, cozy 2-bedroom, 1.5-bath home nestled in SW Hills. Perfectly situated for outdoor lovers and urban explorers alike, you'll be just steps from Forest Park's iconic trails while only minutes from downtown. This charming home is ideal for couples, small families, or business travelers looking for a quiet, comfortable stay surrounded by nature.

4.95 out of 5 average rating, 66 reviews

Guest suite in Northwest Portland

The historic Firehouse No. 17 features a striking brick facade with red detailing and elegant windows. Two large garage doors are framed by decorative patterns, creating an inviting entrance. The building's architectural elements reflect its storied past, surrounded by manicured greenery.

Historic NW Nob Hill Firehouse No. 17

Firehouse No. 17 is a unique and interesting place to stay. The engine bays of the Firehouse have been converted into a beautiful and spacious living area. There are historic photos of the Firehouse that help tell its story from a working firehouse to a fabulous residence. Please come experience this historic firehouse, located in NW Portland. It is an easy walk to bustling NW 23rd restaurants and shops.

4.96 out of 5 average rating, 128 reviews

Guest suite in Northwest Portland

Remodeled 1906 Craftsman home in Nob Hill district

Enjoy Portland from this centrally located, meticulously maintained Craftsman style home. Just steps away from trendy 23rd street, this cozy independent home lets you truly experience Portland. Original character with tasteful upgrades provides both comfort and style to make your vacation memorable. Please note that parking is either in the paid public parking lot or metered street parking only.

5.0 out of 5 average rating, 78 reviews

Popular amenities for Portland Downtown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Portland Downtown

Apartment in Pearl District

A bright living area is filled with natural light from large windows, showcasing views of the city. A 65" smart TV is positioned on a modern white entertainment unit. Two cozy chairs offer additional seating, complemented by a stylish large sectional sofa adorned with soft, textured pillows.

Luxury 2bed 2bath Penthouse

4.89 out of 5 average rating, 46 reviews

Apartment in Pearl District

Modern 3BR Haven • Walk to Pearl District

4.64 out of 5 average rating, 45 reviews

Superhost

4.76 out of 5 average rating, 184 reviews

Near Portland Art Museum + Café & Fitness Center

Private room in Northwest Portland

A spacious guest room features a comfortable bed with a light grey quilt spread across it. Natural light floods in through large windows, offering a view of the outdoors. A dining area with tall chairs and a cozy seating arrangement are also present, creating a welcoming environment.

Nicki’s Million Dollar View Suite @Pdx Downtown

4.86 out of 5 average rating, 227 reviews

Superhost

The entrance of the Heathman Hotel is depicted, showcasing a stylish sign above the door. Planters with neatly trimmed greenery flank the entrance. Pedestrians walk along the sidewalk, reflecting the lively atmosphere of downtown Portland, with shops and trees lining the street.

5.0 out of 5 average rating, 4 reviews

Steps to Powell’s & Art Museum | Pet-friendly. Gym

4.88 out of 5 average rating, 103 reviews

The Clyde by Kasa | King Suite

Hotel room in Portland

Queen Shared Bath

4.86 out of 5 average rating, 188 reviews