Holiday houses in Portland Downtown

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.

Location · Condition · Getting around

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.

Location · Value · Amenities

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.

Location · Value · Condition

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.

Value · Location · Quiet

Cozy artist's bungalow steps from NW 23rd

Designed for comfort by 10-year Superhosts, this 1+ bedroom single-level bungalow is recently renovated, filled with original art and period furnishings, and steps away from Portland’s beloved 23rd Ave. Stroll the quiet, tree-lined streets to the best restaurants, shops, bars and coffee, or hop the streetcar to the Pearl or downtown. Home includes a large gourmet kitchen, off-street parking, and a covered deck overlooking a cottage garden certified as a Backyard Bird Sanctuary.

Location · Family · TV

Elegant NW Portland Suites - Central Walkable Stay

✨ Bright NW Portland Loft Near 23rd Avenue ✨ 🏠 Private entrance, soaring ceilings & modern design 🛏️ Cozy 1-bed setup, perfect for couples 🍳 Full kitchen with coffee maker & wine glasses 🛋️ Smart TV, dining table & fast WiFi 💻 Laptop-friendly workspace for remote workers 🌀 AC, ceiling fan & room-darkening shades 🧺 In-unit washer & dryer — pack light 🔒 Entire loft to yourself, no shared spaces 📍 Steps from NW 23rd shops, cafes & restaurants. Paid parking available.

Value · Location · Laundry

Mid-Century Hillsdale Retreat

Welcome to our chic 2-bedroom, 1-bath Mid-Century Modern retreat, where timeless design meets contemporary comfort. Our fully renovated apartment offers a stylish and inviting space, perfect for your getaway. Enjoy the convenience of walking distance to culinary delights, with City Thai, Gigi's Cafe, and the Hillsdale Food Cart Park just steps away. Immerse yourself in the vibrant local scene, or stay home and utilize the fully equipped kitchen to cook a delicious meal.

Family · Location · Nearby

Queen Anne Guest Apt. In Historic District

Discover a charming guesthouse apartment in the heart of Portland! This private retreat, nestled in a historic home, offers easy access to the city's vibrant scene. Explore the nearby NW 21st/23rd commercial districts, the Pearl District, and downtown Portland. Enjoy delicious dining, unique shops, and exciting entertainment, including the Timbers and Thorns soccer stadium. Perfect for leisure or business travelers seeking a comfortable and convenient stay.

Location · Value · Hospitality

Holiday Home

Welcome to Portland! We hope you have a wonderful time in our beautiful city, and that Holiday Home makes it feel like yours for a while. It's cozy and spacious, with 7 distinct outdoor seating areas for groups of any size — gather together, or peel off for a quieter conversation without anyone feeling left out. After 8 years and 267 stays, this house still surprises people: it's a current Guest Favorite, in the top 10% of homes on Airbnb.

Location · Family · Backyard

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.

Family · Value · Hospitality

1BR - Boutique Flat - Prime NW Location

✨ Stylish NW 23rd Apartment — Portland's Best Block ✨ 🏙️ Steps from NW 23rd's top restaurants & shops 🛏️ Queen bed in private 1BR/1BA 🍳 Full kitchen with stove, microwave & coffee maker 🛋️ Smart TV & fast WiFi for streaming 💻 Laptop-friendly workspace for remote work 🌿 private entrance — your own oasis 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🍽️ Heart of walkable Northwest Portland.

Location · Family · Layout

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.

Value · Family · View