Kid-friendly holiday rentals in Bend

Midtown gem I Cozy Fire I Full kitchen I Park View

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!

Cozy, Quiet Suite in the Country

Come stay at our comfortable shop suite. Our 600 sq ft well-appointed space feels bigger than it is, with beautiful custom details. Relaxing, farm views out every window. Private bedroom, foldout euro lounger in living room. Spacious spa-like bathroom, there's no shower, but you'll hardly miss it for the other beautiful amenities and atmosphere. Kitchenette with the basics, including fridge, microwave, dishes, french press or keurig, and hot water pot. Cozy theater room, perfect for a night in.

800 sf Sunny Private Suite close to Mt. Bachelor

Newly remodeled 1bd guest unit (within a main house) in quiet, private community just 20 minutes from Mt. Bachelor. Surrounded by pine trees, bluejays & herds of deer, and located next to hundreds of miles of mountain biking / hiking trails + bike path to downtown. Prime location for all the outdoor adventures Bend offers, just off Century Dr. which is the road to Mt. Bachelor, Tumalo Mtn, Elk Lake, and hikes galore! We're also 10 mins away from downtown + a short hike to the Deschutes River.

The Guest Nest- quiet convenience in Midtown Bend!

Stay, relax, and rest in The Guest Nest! Delightful, comfortable, well-lighted, and close to everything! Your are at "nest level" in my upstairs apartment. My goal is to provide a welcoming comfortable place for you to stay! ! In return, I request that you treat my Guest Nest with care and respect-- just as you'd want guests in your home to do. You are not dealing with an impersonal corporate rental company. I clean and manage everything myself and do my best to make it perfect for you!

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.

Hillside Haven: Tranquil NW Studio Near the River

Wake up refreshed in this bright sanctuary overlooking a rocky hillside and grassy meadow in an historic neighborhood. Comfy king bed, private entrance, kitchenette, private bath & dedicated workspace. Walk to beautiful First Street Rapids Park footbridge (less than 1 min) & Downtown along the River Trail passing several parks. This unique space has charm along with an ideal location. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.♥︎

Curated Comfort | Quiet, Clean, Beautiful Design

Enjoy modern style and convenience in this recently built guest home. Flooded with natural light, this spacious retreat is in a welcoming neighborhood - the perfect place to relax. Enjoy morning coffee on the sunny porch or walk to Larkspur Trail and Pilot Butte State Park. Explore Mt. Bachelor, the Deschutes River, and Smith Rock, all close by. Downtown is just a quick 5-minute drive. Everything you need is nearby, whether it's fine dining, outdoor adventures, or local shopping.

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

Modern Apartment Perfect For Couples (Dogs Too!)

Adorable and modern apartment bungalow on the east side of Bend with a little private yard, deck, kitchenette, and dedicated workspace. Equipped with everything adults, and pets need to relax, work and explore the beauty and adventure of Central Oregon. The location is ideal with quick access to everything in Bend. Downtown is a 10 min drive, and Mount Bachelor is 30. This 300-square-foot apartment is the perfect home base to explore Bend!