Family-friendly vacation rentals in Southeast 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

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.

Cozy Guest Cottage in Woodstock Neighborhood

A bright and cozy cottage located near Reed College, Woodstock's restaurants/coffeehouses, Trader Joe's and public transit. This residential neighborhood is ideal for a quiet retreat for all visitors. The private guesthouse is outfitted to make your stay comfortable including a spacious bathroom with a walk in shower and a heated floor. Plus, you may want to enjoy a cup of coffee on your own patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Peaceful Apartment in the Heart of Portland

A stellar studio apartment in happening SE Portland. Apartment is attached to a house on a quiet dead end street. BUT... 1 block off trendy SE Division Street, and 8 blocks off SE Hawthorne Blvd. Just a couple blocks to Pinolo Gelato, Salt and Straw, Baghdad Theater and many other popular restaurants, bars and shops. On main bus line. St Parking. Apartment has a kitchenette, full bath, queen size bed, private entrance, private outdoor area, and everything needed for a relaxing stay in Portland.

Sweet Hideaway in the trees, Mount Tabor

Sweet Hideaway is a little, cozy space for couples or solo travelers looking for a peaceful refuge in the trees, yet only a 10 minute drive to downtown. You will have your own entrance and enjoy a Tempurpedic queen bed, a smart TV, your private bathroom, a dining/kitchenette area with a bar table and stools, mini-fridge, microwave, toaster oven, coffee maker, tea, coffee, treats, utensils, a private table and chairs on the deck over the trees. For 2+ night stay, free use of washer/dryer.

Projector/Spacious/Airy ★ Walk to everything!

A modern-elegant 1000 sq ft guest suite, a few minute walk from a gorgeous, 26 acre park and all the restaurants, bars and shopping you could want. The space is complete with a private guest bedroom with luxury, organic bedding, private bath with locally-made products, a fully loaded kitchenette, an 8-seat dining table, a 100" screen with access to every streaming service, lightning-fast wifi, and even a baby-grand piano! Perfect for couples, business travelers or families.

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Hawthorne Hideout*Heated floors* walk everywhere!

This custom one-bedroom basement apartment has full size ceilings and windows and all the comforts of home. Stellar location two blocks from Hawthorne Street. With a kitchenette, washer/dryer, 4K smart TV, and beautiful custom wood and tile throughout. There is radiant floor heating that keeps this space extra cozy in the winter, and cool in the summer. Perfect home base for exploring or working in Portland with or without a car. This space is friendly to all.

Award-Winning Guest House with Private Entrance

Featured in Dwell Magazine; Winner of “Best Whole House Design” by Oregon Home Magazine, this spacious urban garden retreat has one-bedroom with a luxurious king bed, full bathroom, and fully equipped kitchen. Tucked away in a tranquil urban oasis, the space is filled with natural light and boasts a private garden entrance. Wake up refreshed in the crisp, white bedroom and slide open the rustic barn door for a coffee on the patio of this zen retreat.

Cozy and Walkable 1 bedroom daylight basement

Our basement has been newly renovated. Brand new bedroom, beautiful bathroom and living space. The living space includes a 57” Smart TV and couch. The wet bar features a mini fridge, sink and Keurig Coffee maker. The bedroom has 1 queen sized bed with hotel luxury 1800 bedding sheets, a dresser, full length mirror and natural light window. Our house is centrally located with dozens of restaurants, bars and coffee shops just a short walk away!

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! 🏡

Large SE Apartment • Walk to Eats • 1BR • Sleeps 4

If you're a fan of great food, craft beer, and pour-over coffee, this is your place! In the famous Buckman District, my apartment is near Portland’s top-rated restaurants, bars, and vintage shops—perfect for people-watching. Great for couples, solo adventurers, and business travelers, it’s a convenient home base near all the hot spots.