Family-friendly holiday rentals in Bend

Views & Sounds of Deschutes River in Downtown Bend

Entire one bedroom apartment with private entrance from extra large elevated deck with BBQ. Enjoy the view and calming natural sound of the Deschutes River running over the spillway 300 feet away. Easy and secure bike/ski storage. The apartment is a four minute walk to downtown Bend where there are many great restaurants, bars, boutique shopping. You won't find a better location to explore Bend. Electronic locks for easy check-in. Enhanced cleaning procedures. Licensed by the City of Bend.

Cottage in Bend: Walk Everywhere

COTTAGE IN BEND: Cozy 1920’s, one bedroom, one bathroom cottage with a large private yard-blocks from the river and downtown Bend. Enjoy your own space on a large lot-not an ADU. Walk to the market for groceries and coffee on Newport Ave. During your stay walk 3 blocks to the pedestrian footbridge crossing the Deschutes River and into Drake Park and downtown Bend, The Union house is just a block away from Newport Avenue and Newport Market. It is also 3-4 blocks from many restaurants and coffee

Midtown Gem With Cozy Fire and Park Views

Above garage one bedroom/one bath apartment in booming midtown. Open living with a gas fireplace, ac, full-sized kitchen, and gas stove. A large bathroom with a deep tub to relax or let the kids play. The bedroom features a cozy queen bed with a new Tempur-Pedic mattress topper and ample closet space. The east-facing deck is ready to sip your morning coffee while you wake up slowly, grill for an evening in or sit and work with the high-speed wireless as you watch the dog park across the street!

Bend Getaway | 2BR, King Bed, Garage, Fast WiFi

Renovated 2 level townhome, fully stocked, 100% cotton 400 thread count hotel quality sheets. Lives like a house and is the perfect home base for your outdoor adventures in Bend! The primary BR has a comfy King bed & private bathroom. The 2nd BR has a bunk bed (full on the bottom, and a single up top) with private bathroom. Main level features a spacious LR, DR & Kitchen along w/ a 1/2 bath. Located in the Boyd Acres neighborhood, just minutes to downtown and everything Bend has to offer.

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

FLOAT THE RIVER! River, Beach Access Downtown Bend

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.

Parks Bunkhouse

Welcome to The Parks at Broken Top! Paved walking and biking paths run all through the neighborhood, and easily connect to the larger trail systems within Bend. It's only 2 miles to downtown Bend, 1.5 miles to the Old Mill District, and an easy connection to Century Drive which will take you the 17 miles up to Mt Bachelor (usually about a 25 min drive in winter). The private studio/1 bath unit is attached to the main house, but accessed through a shared garage to a private staircase.

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

We are opening up our Aframe to host some visitors to Bend. This Aframe was originally built for the Rajneeshpuram, in Wasco county Oregon in the early 1980's. If you are not familiar with this interesting piece of Oregon history, we recommend you watch the documentary Wild Wild Country on Netflix. It is fascinating. Its a small little dwelling, we have a king sized Mattress in it (no bed frame due the space limitations), with easy access to a bathroom and shower in our home.

The Outpost Bend

The Outpost is a seperate guest home located on our 10 acre hobby farm. It offers spectacular views of the Cascades, stunning sunsets and a peaceful, private location 15 minutes east of downtown Bend. The property adjoins public land, and is on a quiet country road. Our family lives onsite with our 3 sons, dogs, hens, and sheep. The Outpost has a private driveway, use of basketball court, and a lovely private outdoor seating area. 45 min drive to Mt. Bachelor.

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.

Cozy Home w/River Access, Hot Tub, 7min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.

Cabin on quiet 3 acres 10 min to downtown Bend.

Enjoy the peaceful serenity of our guest house. Enjoy a large lawn, irrigation pond with deck for hanging out, and a firepit. Our home is 10 minutes drive to downtown Bend; 45 minutes to Mt Bachelor; 40 minutes to Smith Rock; 20 minutes to Phil's trailhead for mountain biking (All times are without rush hour traffic). Come enjoy all that Bend has to offer!