Guesthouse vacation rentals in Portland

A modern studio house is presented with a light green exterior, featuring large windows and a gray barn door. A stone pathway leads to the entrance, surrounded by a well-kept lawn and garden. A wooden fence provides privacy, enhancing the outdoor space.

4.97 out of 5 average rating, 385 reviews

Studio House-Modern Cozy Gem!

The Walnut Studio House is named after the historic trees surrounding our neighborhood and is carefully designed to maximize your space and provide a relaxing get away. The neighborhood is surrounded by historic homes and trees. Quiet and peaceful yet in the heart of Portland's action--a ‘20 minute’ community where everything you need is walking distance: a beautiful rose garden, locally owned restaurants and bars, food cart pods, groceries, shopping, theaters with music, shows and much more.

Guesthouse in Laurelhurst

A modern kitchen is showcased with sleek cabinetry and stainless steel appliances, including a refrigerator and an oven. A small dining table sits beside a cozy seating area, while a washer and dryer are positioned near the back. Natural wood ceilings add warmth to the space.

4.99 out of 5 average rating, 565 reviews

Little Cedar House High Speed WIFI - Super Clean

5 year old detached guest house in Laurelhurst/North Tabor. Bright and spacious with vaulted cedar ceilings. Modern Industrial style with many eco-friendly features such as mini-split heat/ac, tankless water heater, and all-natural fiber area rugs and linens means fewer toxins and a low carbon footprint. Situated near Laurelhurst and Mount Tabor parks with restaurants and amenities nearby. We are also pet friendly and allow well-behaved dogs on leashes for a $30 fee per dog, per visit.

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.

4.99 out of 5 average rating, 512 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

Guesthouse in Central Northeast Portland

The exterior features a welcoming entrance with a wooden door and modern details. A small patio is furnished with a table and two chairs, surrounded by a wooden fence and colorful autumn leaves. A circular rug adds a pop of color at the entrance.

4.99 out of 5 average rating, 201 reviews

Grant Park Guest House

Newly built guesthouse in highly desirable Grant Park. Beautiful and relaxing one level space with vaulted ceilings, exposed beams, skylights and lots of natural light. All amenities: high speed internet, washer & dryer, full kitchen, memory foam mattress, TV, and private entrance with patio and cafe set. Easy check out! Location is close to everything: great restaurants, food cart pod, Whole Foods, Trader Joe's, Grant park, airport, and more! Walk score of 94. Great space for a get away!

Guest favorite

The entrance to the guesthouse features a warm wooden door framed by lush greenery. Potted plants and a natural wood stool create an inviting atmosphere. Soft string lights hang above, enhancing the serene outdoor space surrounded by trees.

4.99 out of 5 average rating, 253 reviews

Sorta Summer House w/ sauna & outdoor shower

The guesthouse is a private oasis in the city. It's surrounded by fruit trees and tall Chinese Mountain bamboo. It's a quick walk to Woodlawn Park, great coffee, a bakery, pizza, whiskey bar, a brewery, seasonal farmers market, and minutes from Alberta Arts District. The airy, open floor plan is filled with natural light, mixed textiles and warm woods. A cedar-surround outdoor shower and private 5x7 Finnish sauna lend to the spa-like setting. Guests say it’s hard to leave!

5 out of 5 average rating, 250 reviews

A charming guesthouse exterior is framed by lush greenery and colorful flowers. The house features large windows that allow natural light to fill the interior. The welcoming wooden doors add warmth, while a bicycle rests on the pathway, suggesting accessibility to nearby attractions.

Guesthouse in Portland

Perfectly Portland Clinton St Guesthouse

This light & airy guesthouse is a private retreat in a perfect location, steps from Division St. Walkable to Salt & Straw & local eateries, food carts, and thrift shops. Prepare meals in the fully equipped kitchen or head out by foot to Oma’s Hideaway, a 2022 James Beard Award Finalists. Bring your bicycles to enjoy Clinton St Bike Boulevard or stroll to the Clinton St Theater. The guesthouse is family friendly, having special items to accommodate the littlest of guests.

The entrance features a handmade steel pivoting door framed by large planters and greenery. A pathway of concrete slabs leads toward the door, creating an inviting entryway. Soft lighting illuminates the space, enhancing the welcoming atmosphere.

4.97 out of 5 average rating, 402 reviews

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Design, The Green Door PDX was designed to provide a unique respite from the energy of Portland while being conveniently located only minutes from downtown and popular shopping/eating districts. We have taken queues from Europe and built a traditional field cottage tucked into the landscape at the front of the property and surrounded it with mature greenery for an inviting welcome and ultimate privacy for our guests.

Guesthouse in Laurelhurst

A modern kitchen area features white cabinetry and open shelving. A wooden dining table is complemented by sleek white chairs. Natural light enters through large windows, highlighting the clean lines and minimalistic design, while a decorative plant adds a touch of greenery.

4.97 out of 5 average rating, 153 reviews

Modern and Bright Laurelhurst Abode

Our one bedroom cottage is completely private, accessible by a separate walkway, and has an outdoor patio. Extra time was spent choosing finishes and creating a modern, comfortable, and light-filled space. You’ll find everything you need for a weekend in Portland, or a long-term stay. We’ve outfitted a full kitchen, full bathroom with luxurious tub and plush towels, a bedroom with a queen mattress and soft bedding, washer and dryer, and lots of extra touches.

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.

5 out of 5 average rating, 400 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.

The exterior of a guesthouse is shown, featuring a charming wooden facade and large windows. A private outdoor patio is surrounded by lush greenery, including vibrant plants like a red maple and bamboo. A small round table with wooden chairs invites outdoor relaxation.

5 out of 5 average rating, 304 reviews

Colorful, spacious, light-filled guesthouse on MAX

Welcome to Juniper House! We designed our backyard guesthouse to be a bright, cozy loft, full of sunlight, exposed wood, tasteful furnishings and colorful finishes. Enjoy a private, 600-sq-ft space with an outdoor patio in a quiet, close-in Portland neighborhood, just blocks from light rail and within walking distance to a wide variety of great restaurants and watering holes. Perfect for couples and longer stays.

A bright living area is furnished with a gray sofa, two armchairs, and a wooden coffee table. Large windows provide views of surrounding foliage, while natural light fills the space. A small dining table with floral decor is positioned nearby, enhancing the cozy ambiance.

5 out of 5 average rating, 118 reviews

The Canopy Loft PDX

The Canopy Loft is a sun filled, second story studio designed and built by my husband and I to be a cozy home away from home. The window views are full of foliage making you feel like you're up in the trees, hence the name. Our neighborhood is quiet and calm, and we are walking distance from downtown St Johns as well as many parks. The studio can also be turned into your own personal movie theater!

The bedroom features a spacious bed dressed in neutral tones, complemented by a cozy seating area and natural light streaming through large roll-up garage doors. Artwork adorns the wall, while plush throw pillows add comfort to the lounge chairs.