House holiday rentals in Redmond

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.

4.98 out of 5 average rating, 931 reviews

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Superhost

A modern farmhouse exterior showcases a two-story structure with a clean, white facade accented by dark windows and a covered porch. Two red chairs sit invitingly on the porch, framed by a gravel pathway and lush greenery.

4.94 out of 5 average rating, 196 reviews

Smith Rock Hideout - Cascade mountain views

The Hideout is a cozy and convenient base camp for climbers, hikers, trail runners, digital nomads, and anyone wanting to relax and explore the beauty of Central Oregon. Just 8 minutes to Smith Rock! Take in the views of the Cascade mountains and farmland beyond while relaxing on the covered porch. The Hideout is my personal semi-rural retreat. While away, I’m happy to share it with outdoor enthusiasts who enjoy creature comforts after a day of getting after it outdoors. Longer stays welcome!

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, 652 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.

A bright living space is highlighted by large windows allowing natural light to fill the room. Comfortable seating options, including a blue sofa and various chairs, are arranged around a rustic coffee table. A television stands in the corner, enhancing the casual atmosphere.

4.98 out of 5 average rating, 258 reviews

Smith Rock Gardens

You'll enjoy the main house with the best views of Smith Rock and the Cascade mountains. Smith Rock State Park is literally across the street. A great location for outdoor activities at the park or in the region. Hike, climb, bike, walk or jog around the park. Sip tea inside and watch the animals. Perfect for artist and photographers. Relax on the deck or enjoy a sunset BBQ with gorgeous views. Owners live in adjoining unit. Separate entrance. Instagram: @smithrockgardens DCCA Tax# 1784

A spacious wrap-around deck is shown, featuring multiple comfortable lounge chairs facing expansive views of the surrounding landscape. Decorative string lights are hung overhead, adding a subtle touch. The distant mountains are visible against a clear blue sky.

4.97 out of 5 average rating, 182 reviews

Terrebonne~High Desert Hideaway~Near Smith Rock

Thank you for your interest in The Good Earth~High Desert Hideaway. In French Terrebonne means "Good Earth" & it is. Near the world-famous Smith Rock State Park, considered the cradle of US rock climbing. We are convenient to miles of the best hiking trails in Central OR. with views of the Cascade Mtn. Range from a large wrap around deck. An outdoor enthusiasts' paradise~5 mi. Smith Rock State Park, 5 mi. Steelhead Falls Trailhead, 25 mi. Sisters & 29 mi. Bend. Fish~Hike~Birdwatch~Climb

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.

4.98 out of 5 average rating, 323 reviews

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.

The exterior of the bungalow is shown, featuring a light blue facade with a welcoming front porch and a gravel pathway. Lush green grass surrounds the home, complemented by well-kept shrubs and trees. A clear blue sky enhances the inviting appearance of this charming property.

4.92 out of 5 average rating, 132 reviews

Downtown Redmond 3 bedroom

Welcome to this thoughtfully remodeled 80 year old Bungalow that rests in the heart of Redmond, Oregon. A 5 minute walk to fun local restaurants, breweries, bars, live music/concert venues, and eclectic shops. While this adorable home is a perfect vacation getaway, its location makes it very easy for you to get around. You are only: 10 mins to Cline Falls State Park 10 mins to the Redmond airport 10 mins to the Redmond Caves 15 mins to Smith Rock State Park 50 mins to Bachelor Ski Resort

A spacious living area features large glass windows that provide views of the surrounding landscape, including trees and open fields. Comfortable seating with brown leather upholstery is arranged around a central coffee table. Natural light fills the room, highlighting the modern design.

4.99 out of 5 average rating, 295 reviews

Stunning! Smith Rock • King Beds • Steam Shower

A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

A modern kitchen is showcased with a wooden countertop and several metal stools arranged in front. Open shelving holds dishware and kitchen essentials, while stainless steel appliances provide functionality. Large glass doors allow natural light to illuminate the space and offer views of the yard.

4.95 out of 5 average rating, 121 reviews

Dog friendly Home near parks and Dry Canyon

Book your stay today and experience all the comforts of home, with the added bonus of a fantastic location within walking distance to local parks. Located in a quiet neighborhood, it provides a peaceful and tranquil atmosphere. Enjoy a large yard with mature trees, perfect for barbecues and outdoor activities or star gazing in the hammock. The beginning of Dry Canyon trail is only a mile away for walking, running or taking the family for a bike ride. Close to local businesses and dining.

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, 353 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...

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, 456 reviews

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.

The exterior of a charming cottage is displayed, featuring a well-manicured yard with flowering plants and shrubs. A welcoming porch with seating is visible, alongside large windows that bring in natural light. The driveway leads to a landscaped garden area.

4.93 out of 5 average rating, 235 reviews

Rhubarb Cottage - Entire house Dog Friendly!

Dog Friendly! Set in charming Old Town Redmond, this cottage has everything to offer for a quick weekend get away or longer stay with family. Only 25 minutes to downtown Bend and less than 10 minutes to the airport. Featuring 3 bedrooms, 2 full bathrooms, full laundry and a cozy kitchen! Gas bbq, expansive back patio, and corn hole boards to enjoy! Cruiser bikes available to ride to breweries or Dry Canyon Trail just minutes away. 2 Dogs max, additional cleaning fee applies.

Popular amenities for Redmond house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 185 reviews

The single-story home features a natural wood exterior surrounded by tall trees. A spacious front deck includes a dining table with an umbrella and two chairs, providing a welcoming outdoor seating area. The driveway leads to a two-car garage.

Home in Sunriver

Sunriver Home; Hot Tub, SHARC, Fireplace and More!

A private patio features a bubbling hot tub and an umbrella table with chairs. Nearby, a gas grill is positioned for outdoor cooking. Soft lighting enhances the space, while large windows offer views into the cozy interior.

4.97 out of 5 average rating, 228 reviews

Romantic Guest House w/Hot Tub, Pool, Tennis Court

4.97 out of 5 average rating, 209 reviews

A modern kitchen features green cabinetry and a large marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are prominently displayed. Natural light flows in through nearby windows, enhancing the open layout adjacent to a cozy living area.

Home in Sunriver

Walk to Everything! Hot tub, Waterpark passes

Superhost

The exterior of the home displays a two-story structure nestled among tall trees. A wooden deck features a table and chairs, a barbecue grill, and an umbrella for shade, providing an inviting space for outdoor relaxation.

4.88 out of 5 average rating, 179 reviews

Sunriver home 8 SHARC passes, hot tub, wood stove

4.99 out of 5 average rating, 139 reviews

A modern living room is highlighted by a large flat-screen TV and a stylish fireplace. Expansive windows provide views of the outdoors, allowing natural light to fill the space. Comfortable seating arrangements create an inviting area for relaxation.

Home in Sisters

Cozy Mountain Escape: Amazing Views! Hot tub!

A spacious great room features a large sectional sofa facing a sleek fireplace and a wall-mounted TV. Vaulted ceilings with wood beams create an open atmosphere. Expansive windows allow natural light to fill the space, showcasing views of the surrounding greenery.

4.96 out of 5 average rating, 123 reviews

Luxury Sunriver 5BR | 3 Suites! Hot Tub, EV, SHARC

4.93 out of 5 average rating, 122 reviews

The exterior of the modern home features dark blue siding and stone accents, set against a backdrop of tall pine trees. A well-paved driveway leads up to a two-car garage. A warm glow emanates from windows, hinting at the inviting interior.

Home in Sisters

Modern Tollgate Home - HOT TUB | Half Acre Lot

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.

4.95 out of 5 average rating, 114 reviews

Eagle Crest Resort - 3 bdrm home in Central Oregon

Weekly house rentals

4.94 out of 5 average rating, 104 reviews

Two blue Adirondack chairs are positioned on a lush green lawn, overlooking the calm Little Deschutes River. In the background, the river reflects the surrounding trees and grassy areas under a clear sky, creating a serene outdoor space for relaxation.

Home in La Pine

Riverfront/Hot Tub/Dock/Pet Friendly/Game Room

4.96 out of 5 average rating, 171 reviews

An exterior view of a single-story home is shown, surrounded by landscaped gardens with rocks and greenery. A cozy patio area features blue and white striped lounge chairs, an umbrella, and string lights overhead, creating a welcoming outdoor space.

Home in Larkspur

Close, Cute & Clean! *Hot Tub* Bend Adventure Base

An open living space is displayed, featuring sliding barn doors that lead to a bedroom. A large wall artwork of a bridge over a misty landscape adds depth, while a cozy armchair and a small ornate table create inviting seating options.

4.88 out of 5 average rating, 410 reviews

Charming east side house, with hot tub.

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, 122 reviews

Eagle Crest Chalet Hot Tub!

4.99 out of 5 average rating, 201 reviews

The modern exterior of the ADU features wooden accents and large windows, surrounded by lush greenery. A small outdoor seating area with two chairs and a fire pit is visible. The entrance is framed by a wooden fence, providing privacy and inviting atmosphere.

Home in River West

Modern retreat in central Bend

A well-appointed bedroom features a spacious bed draped in striped bedding. Two bedside lamps provide soft illumination on either side, while a large window offers views of the outdoor greenery. A full-length mirror adds functionality to the room's clean design.

4.98 out of 5 average rating, 167 reviews

Best for Old Mill:River Trail, Views & Town

A spacious living area features solid oak flooring and a wood-burning stove set against a stone wall. Large windows offer views of the surrounding trees and snowy landscape, while a cozy stack of firewood is arranged beside the stove.

5 out of 5 average rating, 188 reviews

Lava Rock Retreat Modern Rustic Home

The image captures a stunning sunset over the Deschutes River, with vibrant colors reflecting on the water's surface. A natural arch made of branches frames the scene, enhancing the outdoor space. Lush grass leads to the riverbank, surrounded by tall trees.

4.94 out of 5 average rating, 180 reviews

Deschutes Dreams Riverfront hot-tub, firepit!

Private house rentals

A single-story home is set against a clear blue sky, featuring a light-colored exterior and a welcoming front porch. A well-maintained lawn surrounds the house, with a pathway leading to the entrance and a small seating area visible to the right.

4.97 out of 5 average rating, 31 reviews

Cozy Quiet Getaway - near RDM airport

4.98 out of 5 average rating, 305 reviews

Home in Orchard District

Have a Patio Barbecue at a Pet-Friendly House in Midtown

A spacious dining area is designed with a large wooden table surrounded by black chairs. A striking light fixture hangs above, while brightly colored runners add a vibrant touch. The kitchen is visible, featuring modern appliances and ample natural light streaming in through the windows.

4.96 out of 5 average rating, 28 reviews

Luxury Eagle Crest Chalet + Arcade | 3BRD

4.92 out of 5 average rating, 38 reviews

Home in Larkspur

Private apartment in home

4.9 out of 5 average rating, 10 reviews

Old Mill Treehouse - 5 min walk

A modern retreat is set against a backdrop of native landscaping, featuring expansive windows and a blend of wood and metal exterior. A winding path leads to a cozy fire pit area, surrounded by lush greenery and outdoor seating, providing a serene connection to the high desert environment.

5 out of 5 average rating, 19 reviews

Luxe 4BR/3BA • Smith Rock, 9 Peaks, Hot Tub, 10 Ac

4.88 out of 5 average rating, 26 reviews

Home in Powell Butte

Comfortable and quiet guest house

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.