Family-Friendly rentals near Old Mill District

Modern retreat in central Bend

Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

<SALE> River Front | Hot Tub | Old Mill | Dogs

Enjoy this Contemporary Luxury Home directly on the Deschutes River. Literally step out your back door and stroll, run or paddle up and down the river. The river trail is a 3 3/4 mile loop and one of the best hikes around. Back at home sit on your deck or in the Hot Tub and listen the the sounds of the river going by and enjoy peaceful solitude. Shop or get a bite to eat at The Old Mill, Box Factory, Food Carts and more which are a peaceful 3/4 mile stroll along the river trail. Enjoy!

River Run Bend Bungalow & Romantic Spa Grotto

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

BEST location in Bend! *HOT TUB*

Welcome to Columbia House! Just steps away to Downtown Bend, Drake Park, Galveston Corridor (10 Barrel, Sunriver Brewing, Boss Rambler, The Lot Food Trucks, Westside Tavern, Victorian Cafe and more!), Old Mill (shops and eateries), Hayden Homes Amphitheater - leave your car at home! This updated and spacious home accommodates up to 6 guests and is kid and pet-friendly. We pride ourselves on having meticulously clean vacation homes and top-notch local management to make your stay exceptional.

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

Location! Bungalow River & Beach Access

Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

The Heart Of Bend. Brownstone Apartment.

LOCATION CAN'T BE BEAT Meticulously Clean Modern Space Private apartment STEPS AWAY FROM THE DESCHUTES RIVER AND A 5 MINUTE WALK TO THE SUMMER SHOWS AT THE AMPHITHEATER A PERFECT BASE FOR WINTER AT MT. BACHELOR NO-CONTACT EASY CHECK-IN OLD MILL LOCATION IN THE MOST DESIRED NEIGHBORHOOD IN BEND Perfect setting in the heart of Bend between downtown & The Old Mill District Walk to fine dining, boutiques, galleries, theaters, coffee and the Deschutes River Trail steps away

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.

Drake @ The DUPE - blocks from Old Mill District -

Drake: Located blocks from the Old Mill District, this beautifully updated 2-bed, 2-bath townhouse blends privacy with an unbeatable location. Walk or bike to the Old Mill, Deschutes River, dining, and the Hayden Homes Amphitheater. Tucked in a serene, tree-lined setting, the private home features a bright kitchen with updated appliances, a primary suite with a walk-in tile shower, and a separate porch with a BBQ grill. The perfect mix of modern comfort and convenience.

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway ensuring your privacy.

Central Modern Guesthouse with EV Charger

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.