Family-friendly holiday rentals in Southeast Portland

Cozy Garden Cottage in the Heart of Richmond

A serene Guest Cottage nestled in a garden and located within walking distance to the local foodie restaurants. You’ll love the location and how quiet it is! The perfect set up for couples, solo travelers or business travel. It's open and bright. French doors, plenty of windows, and skylights to bring in natural light for an open feel. You'll be set up with a comfy mattress, quality linens and plush towels. Nothing more cozy than that! Don't forget about the Smart TV, work desk, and essentials!

Family · Indoor spaces · Heating

The Backyard Bungalow! Big Living; Small House

The Backyard Bungalow - featured on Portland's ADU tour - is the perfect hideaway amidst uncertain times. With its own secluded pathway, and detached from the main house, it offers as much privacy as desired. Once inside however, its 16ft vaulted ceiling and sunlit open-plan living area surprises with a sense of spaciousness and comfort. Its inner SE location is walking distance to Division St. restaurants and cafes, food carts, parks and playgrounds, as well as being a "biker's paradise".

Family · Indoor spaces · Backyard

Private Oasis! Cozy & Close to Everything!

Beautiful, one of a kind guest house nestled in one of Portland's most desirable locations! This chic and cozy space features vaulted ceilings, all new appliances, comfortable furniture, and tons of natural light! A quiet street, peaceful atmosphere (and awesome soaking tub) make this the perfect spot for relaxation. Enjoy exploring the surrounding neighborhood and easily walk to shops, restaurants, bars and Laurelhurst Park! Central location allows quick travel to other areas of the city!

Indoor spaces · Kitchen · Value

Chic Belmont retreat w/tree views & king bed!

Experience weird and wonderful SE Portland from a serene, newly-built home in a walkable/bikeable neighborhood with king bed and lots of light! Wake up well rested and open curtain on floor to ceiling windows to morning light. Enjoy the full kitchen & soaker tub in a breathtaking architect-designed home perfect for foodies, couples, and remote work. Great location just steps from bakeries, shops, parks and taprooms. Discover the quirky character and trendy eats of Belmont-Hawthorne-Tabor!

Kitchen · Family · Hospitality

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

Kitchen · Indoor spaces · Value

Woodstock•Net Zero•Chef Kitchen•Firepit•Pet-OK

Private, net-zero 1-bedroom guest house in Woodstock—no shared walls or space. Walk to Double Mountain Brewing, New Seasons, restaurants, and transit, then relax in a fenced yard with a firepit patio. Enjoy a custom kitchen with Sub-Zero fridge and Miele range, endless-hot-water tile shower, and bright modern furnishings. Dogs welcome; self check-in. Sleeps up to 4 with a queen bed, queen sofa bed. Dwell has 18 solar panels that cover more electricity than the building uses!

Indoor spaces · Kitchen · Bathroom

Newly built studio in perfect SE location

A cozy newly renovated space with a modern motif. Plenty of natural light, high ceilings. Large walk in shower,walk in closet, washer +dryer and kitchenette with microwave. Queen size bed with European style bedding:fitted sheet, pillows and king size duvet with duvet cover, NO FLAT SHEET or TOP SHEET. The apartment is located in one of the best neighborhoods on the east side.Close to downtown, bus lines, bikes and scooters rental,shopping,casual and fine dining.

Family · Kitchen · Backyard

Mt Tabor Tree House, Hidden Urban Retreat

Our Mt Tabor Treehouse is an incredible and unique escape that invites you to relax and connect with nature without sacrificing any modern amenities, all in the heart of the City of Roses. Nestled underneath towering Douglas Fir trees, this fully equipped tiny house in a tree is surrounded with nature, along with immediate access to miles of mixed use trails and walking distance to one of Portland’s best restaurant, coffee shop and local market “Coquine”

Family · Kitchen · Cleanliness

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.

Kitchen · Family · Parking

Modern Hawthorne 1BR - Food Carts & Local Shops

✨ Compact 1BR Hawthorne Hideaway for Two ✨ 🛏️ Cozy 1-bedroom with queen bed 🍳 Full kitchen with stove, oven & coffee maker 🧺 In-unit washer & dryer 💻 Laptop-friendly workspace with fast WiFi 🐾 Pet-friendly - bring your furry friend ❄️ Living-room mini-split A/C + heat 🚪 Private entrance - no shared interior spaces 🍽️ Heart of Hawthorne - cafes, brewpubs & shops nearby. Free street parking.

Kitchen · Indoor spaces · Hospitality

Portland's Best in Hawthorne District

Step outside and explore the charm of Portland's Hawthorne neighborhood, filled with vintage shops, local bookstores, and cozy coffee spots full of character. Stroll past colorful murals, browse unique boutiques, and take in the laid-back, creative vibe. Whether you're here to relax, explore, or a little of both, this welcoming space is a great place to call home through your stay.

Kitchen · Indoor spaces · Layout

Stylish Hawthorne 1BR w 90 WalkScore

✨ Walkable Hawthorne 1BR with Fast WiFi ✨ 🛏️ Cozy 1-bedroom with queen bed 🍳 Full kitchen with dishwasher & coffee maker 🛋️ Cable TV & fast WiFi 💻 Laptop-friendly workspace for remote work 🐾 Pet-friendly - bring your furry friend ❄️ Living-room mini-split A/C + heat 🔒 Private entrance - entirely yours 🍽️ Steps from Hawthorne cafes, brewpubs & shops. Free street parking.

Kitchen · Family · Hiking