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

Cozy, Light & Bright Private Guest Suite + Hot Tub

Our private guest suite is filled with natural light, a comfy queen bed and kitchenette. Ideal stay for a short getaway or just passing through. Outside the suite you’ll find a covered patio space perfect for a morning cup of coffee or evening glass of wine. To relax, take advantage of the 6-person hot tub and gas fire pit. The location is just 3 minutes from downtown, 10 minutes to Redmond Airport, 20 minutes to Smith Rock, 20 minutes to Bend, approx. 50 minutes to Mt Bachelor and Hoodoo.

Adams Corner, WiFi, courtyd w/games Sewist access

Adams Corner is a space that a visitor will find inviting, comfortable, and private. Located in a quiet neighborhood, we are pet friendly with a securely fenced yard and near a park that is great for walking your pet. Less than 5 minutes away from the Hwy 97 on-ramp that takes you to Terrebonne and Smith Rock, or connects you to hwys to Bend, Prineville, and Sisters. We are a few minutes away from Walmart, We are available on site to answer questions and provide information about the area.

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.

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

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.

The Little Red Chimney House - 3 BR 2 BA

Originally built in 1944, this is a wonderfully furnished bungalow with 3 queen bedrooms and 2 full bathrooms, which I completely renovated and remodeled. It is a stone's throw from Fred Meyers grocery store and Cascade Lakes Brewery, and within easy walking distance to downtown. This house is at the hub of Central Oregon and sits at the crossroads between Bend (14 miles), Prineville (20 miles), and Sisters (20 miles) and is 10 miles from Smith Rock and 2 miles from the Airport.

Greenside 3 BdRm + Hot Tub Chalet in Eagle Crest

Welcome! Come to relax or adventure while staying at our rustic chalet. Located in a prime location at the end of the street, this chalet has everything you will need to enjoy your time away from home. Get cozy inside by the fire, or enjoy the sunrise and sunset on the secluded deck overlooking the 14th green and Cascade Range. Adventurers can venture out to enjoy the sports center, award winning golf courses, and more! The Eagle Crest Resort has fun for the whole family.

"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!

Downtown Redmond Loft

Experience the joy of our space! We've poured our hearts into making sure you feel perfectly at home and cared for. Located in the vibrant heart of downtown Redmond, our house is nestled amidst the beauty of Dry Canyon's parks and the bustling energy of breweries, restaurants, food carts, and shops. 5-minute drive to the airport, 15 minutes to Smith Rock, and 20 minutes to Bend. We're thrilled to host you! Cheers, to your stay! JoHanna

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.