House holiday rentals in Portland

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

Lovely NE bright hideaway, walk to food/beer/shops

Welcome to your Portland Hideaway! This charming 2-bedroom, 1-bath home is the perfect base for exploring the city. Located in a vibrant neighborhood, you're just steps away from Portland's best bars, restaurants, shopping, and parks. Enjoy the convenience of nearby outdoor recreation, with hiking trails only a short drive away. The home features a fully equipped kitchen, cozy living area, and fast Wi-Fi. Whether you're here to relax or explore, this is the ideal spot to experience Portland!

Cozy modern staycation workplace close to downtown

Entire space is very private. Enjoy the cozy modern 1 bedroom queen bed, 2 large sofas that are comfortable to sleep on, oversize soaking tub large walk-in closet , 2 TVs, Blue Ray player, stereo, gorgeous private garden with table seating & tranquil water feature, & private entry. 5 minute drive to downtown, 2 minute walk to Forest Park & Marquam trails. Several amazing restaurants just minutes away. There is a pet fee of $40 each pet. Preferably just one pet or the fee is $70 for two.

Hidden Garden Cottage

This 850 sf. cottage is a century old but was completely updated 12 years ago with era-appropriate furnishings, giving it a period (and safe) feel. Breakfast goodies, art, books, and a woodstove make it cozy. It sits on half an acre so lots of room for kids . It's in SW Portland, minutes from downtown. It's quiet, great for working or vacationing. An outdoor fire pit and gardens make it unique. There's even a zip line for kids. Family gatherings also fine. (Note: There is a $60 fee per dog.)

Alberta Arts Luxe 2 bed 2 bath with AC

Enjoy the true Portland vibe in the upstairs unit of this BEAUTIFULLY and COMPLETELY renovated LUXURY heritage duplex home. Designed to accommodate modern day life. Private entrance through a shared vestibule, Chef's kitchen, AC, DW, strong Wi-Fi, front load W/D, California closets in both BR's. New 4k smart TV's in master bedroom & great room. Perfect sleep on deluxe king or queen beds. Located in the amazing Alberta Arts / Concordia area. Close to everything. 86 walk & 80 bike score.

Rock N Roll House + Hot Tub

Featured in The Destination Channel’s TV show “Staycation- Sports Edition” in the fall of 2025 and found on YouTube. Contemporary-style music-themed home. Jam out with instruments, classic albums and record player by the pool table. Stunning gourmet kitchen. Big lawn and deck with teak dining table and bbq. Hot tub plus gas and real fire pits. Garage is packed! Ping pong table, pinball, foosball, Pop-a-Shot basketball, Treadmill, Peloton bike, dumbbells, and four mountain bikes+helmets.

Designer curated Mississippi home NO CLEAN FEE

Blocks away from Mississippi Ave, this darling designer/ curator owned home is the perfect base for your Portland adventures. Recently renovated, this 1927 home features old Portland charm, contemporary finishes and art covering most every wall. Walkable to everything that Portland is renowned for: restaurants, breweries, coffee roasters, music venues and shops. Minutes from City Center via very close public transportation, bike or car share. The basement in-law suite is owner occupied.

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

Casa Dolce Casa / Home Sweet Home in Alberta Arts

Welcome to my charming detached guest house, filled with touches inspired by my home country, Italy. Experience the quaint charm of a tiny house with the comfort and openness of a traditional home. Stroll to Alberta Arts District's restaurants, bars, breweries, food cart pods, and unique local shops. Explore the Oregon Coast, local hikes, and wineries. Public transport is nearby for city exploration, and the airport is just a 12-minute drive away.

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.

Quirky Micro Apt - Foodies, Artists, Coffee

✨ Stylish SE Portland Cottage in Hawthorne District ✨ 🏡 Private entrance — no shared spaces, entirely yours 🛏️ Cozy 1-bedroom retreat for two 🍳 Compact kitchen with cookware & coffee maker 📺 Smart TV & fast WiFi for streaming 💻 Laptop-friendly workspace for remote work 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🚗 Steps from Hawthorne's cafes, restaurants & shops. Free street parking.