Family-friendly vacation rentals in Redmond

Cozy Downtown Redmond Cottage

Welcome to our cozy Redmond cottage, located in the heart of downtown! Enjoy walking to local breweries, restaurants, and shops, all just steps away. This inviting space offers a perfect blend of comfort and convenience, ideal for couples or solo travelers. Unwind in the cozy living area after a day exploring Central Oregon. Experience the best of Redmond right outside your door! Conveniently close to: 15 minutes to Smith Rock 25 minutes to Bend 8 minutes to Deschutes County Fair & Expo Center

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

Smith Rock Contemporary

Epic views await at this new contemporary Airbnb suite. Situated atop Cinder Butte, with stunning views of Smith Rock, Mt. Hood, Mt. Jefferson and the Terrebonne valley. Enjoy this 800 sf daylight basement apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A covered deck with magnificent views will make you feel right at home. Start your day with a gorgeous sunrise over Smith Rock

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Close to Smith Rock, Mountain View, Country Charm

The Tiny House at Aspen View Farm is just what you need! Great location for exploring beautiful Central Oregon - Smith Rock is only 15 min away. On a unique 14 acre farm, relax and retreat with tranquil Cascade Mountain and country views, say hi to Roo the farm dog, and watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, a/c, heated floors & more! Please read full listing before booking so there are no surprises :)

Downtown Redmond Retreat

Welcome to our charming retreat nestled in the heart of Downtown Redmond! Situated in a quit neighborhood and numerous parks in the Dry Canyon and the vibrant energy of downtown's breweries, restaurants, food carts, and shopping, convenience is at your fingertips. Just a quick 5-minute drive to the airport, 15 minutes to Smith Rock, and 20 minutes to Bend, our location offers easy access to nearby attractions. Step out of your front door, and adventure awaits in every direction...

Blossom Cottage Studio

Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

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.

"Little Pine Cabin" attached to my home.

MASTER SUITE Go hiking, fishing, sight seeing and enjoy upscale steak houses, Sushi Bars, food carts, all within a couple of miles. Then come back to your Little Pine Cabin. Enter into a comfortable living area with a vaulted knotty pine ceiling, propane stove, a dual reclining leather couch. Relax in front of the 42 inch flat screen, a well stocked coffee bar, microwave and a mini-fridge. Similar to a studio apartment. You will enjoy the space and quiet neighborhood.

1918 Bungalow | Modern Renovation•Walk to Downtown

Beautifully restored 1918 bungalow in the heart of Downtown Redmond. Walk to local brewpubs, coffee shops, and food carts. Just 17 miles to Bend. Enjoy luxe linens, plush towels, a soaking tub, and a fully equipped kitchen. Immaculate, cozy, and full of character—this historic gem blends comfort, style, and walkable charm for a memorable stay. Steps from local favorites—food, drinks, and downtown vibes! Perfect base for exploring Smith Rock, and Central Oregon beauty!

Wow Holy Cow Chalet

Wow Holy Cow! will be your first thought when you set foot into this knotty pine walled, sunlit filled chalet. Furnished with everything you need for a fun, family getaway. Channel Maria von Trapp while taking in the beautiful mountain views from the loft space. Have a drink on the deck while your kids search for frogs in the rock feature and shallow creek below. Grill a steak on the bbq and admire the deer who often pass by. DCCA# 1453

Modern Downtown Cottage near Outdoor Adventure

Nestled in the heart of Downtown Redmond, this beautifully designed cottage offers the perfect blend of convenience and comfort. You'll find yourself within walking distance of charming coffee shops and restaurants, and just 14 minutes away from the breathtaking Smith Rock. The Redmond Airport is less than 10 minutes away, and if you're planning a visit to Bend, you can be downtown or floating on the Deschutes River in under 20 minutes.