Family-friendly holiday rentals in Portland

Hawthorne Hobbit Hole: special Portland experience

The Hobbit Hole is a cozy, comfortable sculpted suite to stay. It's an enchanting oasis, crafted with love and with guests in mind. This is a walking, biking, and transit paradise with easy curbside parking. We are around the corner from an organic grocery store, iconic restaurants, shopping, bike share programs and entertainment on perfectly Portland Hawthorne and Division streets. We are an open and affirming household who welcomes all. We do allow smoking/vaping outside, including cannabis

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.

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

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.

Inner SE PDX! Historic Sellwood Basement Apt

Welcome to a 1912 landmark home in beautiful Sellwood/Moreland. Formerly the beloved Candyland restaurant, the light and bright basement apartment sits in front of the Springwater trail with views of Mt Hood. This is a 1 bedroom with kitchenette (stove burner and mini toaster oven) living room and dining room fit for 3! We are close to great shopping, dining and breweries get there by bus, the Max or bike in minutes. We welcome you to a safe and inclusive home and we are vaccinated!

Portland Tiny House

Welcome to Portland Tiny House! Featured in Airbnb Magazine, this cozy spot is located in the Alberta Arts District, just steps away from award-winning restaurants, cafés, bars, art galleries, and shopping. You can reserve time at the Kennedy School soaking pool or catch a movie at their theater, enjoy a craft cocktail at Expatriate, take a yoga class at People’s Yoga, or shop the local New Seasons Market. A popular Portland neighborhood to make your home base for a memorable stay!

Garden Home Backyard Yurt Experience

Our cozy-comfy 4 season yurt is nestled under majestic trees on a beautifully landscaped 1/3 acre. Located in a quiet, safe SW Portland neighborhood with a park, hike/bike trail a block away. We are 6 miles from downtown, with beaches, gorge and Mt. Hood accessible for day outings. There is a full kitchen, a natural gas fireplace and complete electrical and plumbing service. The guests full bathroom is located in the home's utility room a short lighted pathway walk from the yurt.

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.

The Royal Scott Double Decker Bus

Our tiny home started life as a commuter bus in Manchester, England, in 1953, then did stints in San Francisco and Mt. St. Helens before finding a home as the Grilled Cheese Grill in Portland. Now it’s been reimagined as a mid century modern-inspired tiny home, with whimsical painting details from one of its former lives and fresh new handmade details that make it a cozy, inspiring stay. Find more on IG @smore.life

Cozy Studio In NE PDX (Cully/Beaumont-Wilshire)

Cozy (240 sq ft), private studio space located in NE Portland on the edge of the Cully and Beaumont-Wilshire neighborhoods. We are located on a bike route and about a 12-minute walk to NE Fremont Street (many restaurants, coffee shops, bars), 12 min by car to the airport, and 15 min to downtown. Small kitchenette with microwave, mini-fridge, toaster oven, and coffee/tea supplies. Queen bed, super comfy mattress.

Monta-Villa Garden Cottage & Furry Farmstead

Private cottage with views of the garden & cats. High ceilings, lots of natural light & warm accents. 🥰 Four, friendly cats and four, suspicious hens in the garden chickens coop. 🐈‍⬛🐓 Tranquil garden with bubbling fountain, chimes, & sheltered, cozy seating. ⛲️ Nearby food, drink, shopping & recreation options. 🍷 Local recommendations. 🌟 Ask about renting our Toyota Sienna. 🚐 Your home away from home! 🏡

Hawthorne Wisteria Retreat

A private studio in a garden courtyard located in the heart of bustling Hawthorne and Division neighborhoods, this retreat offers walking access to countless top restaurants, boutiques, vintage stores, book stores independent movie theaters and more. There is ample street parking right infront of the house or very near.