Family-friendly holiday rentals in Redmond

A cozy living area features a grey sofa adorned with decorative pillows, positioned on a textured area rug. A flat-screen television is mounted on the wall, while a stylish black stove adds warmth. Natural light enters through a nearby window, enhancing the space.

4.92 out of 5 average rating, 116 reviews

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

4.92 out of 5 average rating, 145 reviews

HOT TUB, Eagle Crest Condo on Golf Course, DOGS OK

This beautiful condo is located in the desirable resort community of Eagle Crest which is home to three 18-hole golf courses, an 18-hole putting course, and miles of trails. There is a private hot tub on the back deck that backs up to the golf course, as well as a BBQ. There are 2 spacious upstairs bedrooms each with their own private attached bathroom and walk-in closets. Downstairs is a fully stocked kitchen, propane fireplace, and dining area/table. Come enjoy all Eagle Crest has to offer!

A living area features a dark leather couch and a patterned armchair, centered around a wooden coffee table. Natural light filters through the window, illuminating the warm tones of the room. A landscape painting hangs on the wall, enhancing the inviting ambiance.

4.84 out of 5 average rating, 688 reviews

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.

4.97 out of 5 average rating, 370 reviews

A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.

Home in Terrebonne

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.

5 out of 5 average rating, 284 reviews

A bright living area is filled with natural light from large windows. The cozy sofa offers a relaxed seating option, complemented by a stylish ottoman. A well-equipped kitchen features modern fixtures, and exposed wood details enhance the warm and inviting ambiance.

Tiny home in Redmond

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 :)

A dining area is highlighted by a rectangular table surrounded by four upholstered chairs. A soft, neutral carpet covers the floor. Natural light filters through a window draped with dark curtains, while a textured brick wall adds warmth to the setting.

4.96 out of 5 average rating, 373 reviews

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...

4.92 out of 5 average rating, 155 reviews

A cozy seating area is presented with a gray armchair beside a small white dining table. A decorative mirror and greenery adorn the wall, while sunlight filters through a nearby window, illuminating the space. A rug adds warmth to the wooden floor.

Cottage in Redmond

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.

4.9 out of 5 average rating, 272 reviews

A studio cabin is positioned on a deck overlooking a canyon, surrounded by native plants. Two wooden chairs are placed on the deck, providing a space to absorb the expansive mountain views in the distance. The structure features a large window reflecting the evening light.

Cabin in Culver

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.

A cozy living area features a leather couch facing a propane stove, with a warm fire flickering. Two wooden stools are positioned at a small table, and a stack of magazines is displayed on a wooden coffee table. Natural light filters through the window.

4.95 out of 5 average rating, 715 reviews

"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.

4.92 out of 5 average rating, 639 reviews

The living room features a combination of modern and rustic decor, including a brown leather sofa, a wooden coffee table, and a cozy area rug. A flat-screen TV is mounted on the wall, with large windows allowing natural light to brighten the space.

Bungalow in Redmond

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!

Campervan/RV in Terrebonne

A vintage camper is seen under a clear night sky, adorned with string lights that create a soft glow. A campfire ring is positioned in the foreground, surrounded by natural stones. Nearby, a shower house can be seen, also illuminated, with outdoor seating available.

4.97 out of 5 average rating, 152 reviews

Tin Can Ranch

Welcome to Tin Can Ranch! Kick your legs up and enjoy the sunset at Tin Can Ranch where your worries drop away like the leaves in Autumn! Our cozy Vintage Yellowstone "Tin Can" camper is nestled in it's own corner of our 5 acre property located in Terrebonne, OR just a 10 minute drive from Smith Rock State Park and within an hour of the very best outdoor adventures in Central Oregon! Next to the camper is the shower house/bathroom with an outdoor washing sink.

4.98 out of 5 average rating, 306 reviews

A modern living space features a light-filled open layout, showcasing a comfortable gray sofa with coordinating pillows. A stylish wooden coffee table complements the area. The kitchen, equipped with sleek cabinetry and appliances, is visible in the background, promoting a functional and inviting atmosphere.

Guesthouse in Redmond

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.

Popular amenities for Redmond family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 144 reviews

The front exterior of the newly constructed home features a welcoming entrance with large glass doors framed by warm lighting. A landscaped pathway of stones leads to the entrance, surrounded by gravel and desert flora, under a colorful twilight sky.

Home in Bend

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

4.98 out of 5 average rating, 965 reviews

The lookout tower is framed by green trees, featuring multiple wooden decks and a spacious entryway. Steps lead up to the main entrance, and large windows provide glimpses of the interior overlooking the natural landscape.

Home in Terrebonne

Cozy Three Story Lookout Tower

An inviting chalet exterior is highlighted by large windows and a peaked roof, showcasing an open deck with seating. Soft lighting from within creates a warm ambiance against the dusk sky. The surrounding grassy area and stone pathway contribute to the serene outdoor setting.

4.93 out of 5 average rating, 138 reviews

Eagle Crest Chalet Hot Tub!

4.94 out of 5 average rating, 114 reviews

Creekside Escape at Eagle Crest Golf Resort

A shaded deck area features a striped umbrella over a black dining table with four chairs. A private hot tub is positioned to one side, and expansive views of green fairways and tall trees are visible in the background.

4.89 out of 5 average rating, 296 reviews

Eagle Crest-w/private hot tub/Resort passes!

4.9 out of 5 average rating, 315 reviews

An A-frame interior features warm wooden paneling, with a cozy seating area highlighted by a stylish armchair and a television unit. The open door reveals a view of the outdoor pathway, surrounded by greenery, bringing natural light into the space.

Tiny home in Bend

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

Guest suite in Powell Butte

Two Adirondack chairs are positioned on a patio, facing a stunning sunset over distant mountains. A small table is located between the chairs, accompanied by a flower pot. The sky is painted with hues of pink, orange, and purple, creating a serene atmosphere.

4.96 out of 5 average rating, 253 reviews

Panoramic Mountain View Oasis

4.97 out of 5 average rating, 348 reviews

Chalet in Redmond

Wow Holy Cow Chalet

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 583 reviews

A rustic log cabin is nestled among tall pine trees, featuring a welcoming porch with wooden railing. Sunlight filters through the branches, illuminating the surrounding forest floor and creating a serene atmosphere in the natural setting.

Cabin in Bend

Log Cabin on Tumalo Creek

4.85 out of 5 average rating, 373 reviews

A modern living area features a spacious gray couch and a dining table with white chairs. A vibrant abstract painting adds color to the wall, while a fully equipped kitchenette is visible in the background with blue cabinetry and natural light streaming through large windows.

Tiny home in Bend

The Big Tiny

4.96 out of 5 average rating, 283 reviews

The cozy bedroom features a rustic wooden bed frame with soft linens, complemented by natural light from a nearby window. A stylish soaking tub is presented with a wooden shelf nearby. The kitchen showcases modern appliances with a striking blue cabinetry, while a snowy mountain landscape is displayed outdoors.

Home in Bend

Romantic Farmhouse near Mt. Bachelor

4.79 out of 5 average rating, 229 reviews

Luxurious 5 bedroom w pool table

Superhost

The living area features a brick fireplace as a focal point, surrounded by comfortable seating options. A coffee table sits in front of a couch with a soft throw. Natural light enters through large windows, and a door leads to the exterior.

4.87 out of 5 average rating, 490 reviews

The Little Red Chimney House - 3 BR 2 BA

Superhost

A colorful hammock is suspended from a snow-covered tree, inviting relaxation. The quaint WeeHouse, featuring large windows and a bright yellow door, is partly obscured by the snow. A serene winter landscape surrounds the property, showcasing the tranquility of the setting.

Tiny home in Bend

4.84 out of 5 average rating, 268 reviews

IT'S A WEE HOUSE

5 out of 5 average rating, 147 reviews

An inviting hot tub is positioned alongside a sauna grotto, both nestled within a natural setting. The hot tub features clear water with soft illumination, while the sauna's wooden exterior is accentuated by warm light. Surrounding trees and rocks enhance the tranquil atmosphere.

Bungalow in Bend

River Run Bend Bungalow & Romantic Spa Grotto

A private saltwater hot tub is positioned on a wooden deck, surrounded by lush green grass. Two comfortable seating areas, including a wooden Adirondack chair and two cushioned chairs, are available nearby, providing a relaxing outdoor space.

4.85 out of 5 average rating, 189 reviews

Private HotTub | Course Views | Rec Passes +Bikes

Family-friendly home rentals with a pool

A spacious living area is enhanced by large windows allowing natural light to fill the room. A comfortable sectional sofa is complemented by accent pillows. A dining table for six stands nearby, while the cozy fireplace and wall-mounted TV add a modern touch.

4.88 out of 5 average rating, 102 reviews

3 Kings on the 12th Green! Large resort home

4.9 out of 5 average rating, 187 reviews

The living area features leather sofas arranged around a stone fireplace, providing a cozy gathering space. An entertainment unit houses a flat-screen TV, while warm lighting enhances the wood accents. A decorative area rug adds texture to the carpeted floor.

Chalet in Redmond

Eagle Crest Luxury Chalet w/Private Hot Tub&Garage

4.93 out of 5 average rating, 102 reviews

Sunsets, Mt View’s, Private Hottub & Stars!

Cabin in Crooked River Ranch

4.93 out of 5 average rating, 131 reviews

Classic Cozy Cabin with Awe-inspiring Views

4.97 out of 5 average rating, 186 reviews

An indoor pool room features a heated dipping pool, surrounded by vibrant red lounge chairs. A seating area is present with a couch and decorative pillows, while bright artwork adorns the walls. Sliding glass doors allow natural light and lead to the outside.

Home in Bend

Indoor Pool, Game Room, EV Charger, Pets Welcome!

4.94 out of 5 average rating, 106 reviews

An open room features vaulted ceilings and large windows, allowing natural light to fill the space. Two surfboards are artfully displayed on the wall, while a circular dining table and four chairs are positioned in the center. A black office chair is visible at a desk, enhancing the work-friendly atmosphere.

Apartment in Bend

Wine Down and Play

Superhost

5 out of 5 average rating, 3 reviews

Sagewood at Eagle Crest | Hot Tub | Golf

The exterior of a charming home is showcased, featuring a warm-toned siding with multiple windows. The front porch is covered, providing a welcoming entrance. Lush green shrubs and trees surround the property, enhancing the serene outdoor setting.