Family-friendly vacation rentals in Portland

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

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.

Centrally-located 1-bedroom escape in NE

This centrally-located apartment in Grant Park/Hollywood is bright, clean, and cozy. Airport is 6 miles away! 97 Walk Score with luxe amenities: King TempurPedic mattress, full kitchen, dining nook, washer/dryer, designer decor, free street parking, and non-toxic products for body, laundry, and cleaning. Our family lives upstairs full-time but we respect your privacy. IMPORTANT: No same-day or 1-night bookings, no parties, no pets, no smoking/vaping. Must have solid history of positive reviews.

Clinton St Guesthouse • Walkable & Artistic

Stylish Clinton St guesthouse steps from cafés, bakeries, and transit. Features unique hand-painted floors, local Portland art (including child artists), and a small library of Portland authors. Queen bed, blackout shades, AC, desk, fast Wi-Fi, washer/dryer, and a coffee station with Moccamaster, grinder, AeroPress, French press, pour-over, and local beans. Walk to Salt & Straw, Loretta Jean’s, Insomnia Cookies, New Cascadia (gf bakery) Oma’s Hideaway, Cibo, Someday, The End, and food carts.

Eclectic cottage & sauna bath house/SE Portland

This cottage is a rustic bohemian experience. There is a queen bed and a sleeping loft which is good for kids accessed via a built in ladder (one bed and one ikea double mat (great for kids) in total). Cottage has a kitchenette in the main room where the bed is. There is an OUTDOOR shower/bath and sauna which is incredible in the fall and winter! Inside the cottage there is small bathroom which is in fact down right tiny (not for big folks) wood stove/ oil heater/ac. no smoking allowed.

Monta-Villa Garden Cottage & Furry Farmstead

Private cottage with views of the garden. High ceilings, lots of natural light and warm accents. Stocked kitchenette. Four, friendly cats waiting to visit in the garden and three, suspicious, but friendly, hens in the chicken coop. Tranquil garden with fruit tees, flowers, bubbling fountain, chimes, and sheltered, cozy seating. Nearby food, drink, shopping and recreation options. Local recommendations. Your home away from home! Ask about renting our 2023 Toyota Sienna, hybrid minivan.

Jason & Susie's private guest suite w/ kitchenette

Located in NW Portland, our space is in a quiet neighborhood, next to a park and tennis courts. We are 7 minutes from the Nike Headquarters, 2 minutes from Columbia Sportswear Headquarters, and 15 minutes from Intel, making it a perfect stay for your business needs. We are within walking distance to a grocery store, pubs, small restaurants, and the Saturday Cedar Mill Farmers Market. Close by is the entrance to Forest Park, one of the largest urban parks, with 80 miles of trails.

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.

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.

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, cable TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

Handcrafted Urban Hideaway | Private Driveway

Stay in this handcrafted rustic-industrial studio featuring reclaimed wood walls, 15-foot vaulted ceilings, and thoughtful custom details throughout. Private entrance and driveway, 10-minute walk to MAX light rail, and under 25 minutes to Mississippi Ave. Enjoy high-speed WiFi, a well-appointed kitchenette, and all the comforts of home in this unique urban Portland hideaway.

Cozy North Portland Urban Oasis

Super cute and spacious Art Deco private unit with large yard and easy access to St Johns, Overlook, and Portsmouth neighborhoods, as well as the University of Portland, and the Adidas campus. Across the street from Columbia Park and a short walk/drive to excellent bars, restaurants, coffee shops, and other venues. Quiet, relaxing locale perfect for up to four guests.