Vacation rentals in Redmond

4.87 out of 5 average rating, 278 reviews

An open living space is visible, featuring a comfortable black couch with a plaid throw. A modern kitchen area with stainless steel appliances is seen, along with a dining table in the background. Warm wood flooring enhances the inviting ambiance.

Guesthouse in Terrebonne

Near SmithRock pets ok private heated bungalow

close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

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, 656 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, 543 reviews

A spacious outdoor deck is furnished with two Adirondack chairs facing a circular fire pit. A panoramic view of distant mountains and valleys is framed by a railing, showcasing the landscape under clear blue skies.

Apartment in Redmond

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

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, 329 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.

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, 310 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.

4.98 out of 5 average rating, 208 reviews

A small balcony is visible, featuring two woven chairs and a round blue table. Panoramic views of the surrounding landscape and distant trees can be seen, with clouds casting soft shadows over the scene and sunlight filtering through the open space.

Apartment in Redmond

Mountain View Suite near Smith Rock - Fast Wi-Fi

FAST INTERNET. Quiet rural location a few miles from town on rimrock over a small canyon. Enjoy a wide view of the Cascades from a roomy studio apartment that is comfy and uncluttered. Features a big bathroom, walk-in shower, a small balcony, many windows, and a large walk-in closet. On request for additional $35 per stay: roll-away bed. Nearby attractions: 1) Smith Rock State Park-7 mi 2) Dry Canyon trail-1 mi 3) Redmond Airport-6 mi 4) Redmond-5 mi 5) Sisters-23 mi 6) Bend-22 min

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, 243 reviews

IT'S A WEE HOUSE

Quiet, serene, warm and cozy. Relax in this cute little pet friendly WeeHouse with a wee loft. Located in the heart of Central Oregon just minutes from downtown Bend and the Redmond airport. You'll enjoy countryside views of Smith Rock and the valley below. Bask under 1000 year old Juniper trees. High Speed wifi, private bathroom and kitchenette. If this doesn't feel like a fit or is unavailable please check out our other options: "The Sunset Bungalow" and "The Sunrise Studio"

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, 355 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, 461 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.

4.89 out of 5 average rating, 228 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.

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, 239 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.

4.92 out of 5 average rating, 630 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!

Popular amenities for Redmond vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Redmond homes

4.94 out of 5 average rating, 121 reviews

The exterior of the newly constructed home showcases a modern design with a front porch illuminated by warm lighting. Large windows frame the entrance, providing views of the surrounding natural landscape. The property features rocky landscaping with sparse vegetation and a hot tub visible to the side.

Home in Bend

Brand new home* Hot tub* Mountain Views* Sleeps 8

A view from the lodge path shows a wraparound deck overlooking the Marsupial rock formations. Dense trees provide shade, while the high desert landscape is dotted with shrubs and rocky terrain. The clear sky enhances the natural beauty of the surrounding area.

4.94 out of 5 average rating, 162 reviews

Fallen Snag Lodge next to Smith Rock State Park

4.98 out of 5 average rating, 185 reviews

Home in Orchard District

Butler Corner - New, Clean & Minutes From Downtown

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, 934 reviews

Cozy Three Story Lookout Tower

Superhost

4.94 out of 5 average rating, 197 reviews

Smith Rock Hideout - Cascade mountain views

4.98 out of 5 average rating, 129 reviews

Home in Old Bend

A Stone's Throw | Riverfront Retreat | Waterfront

The front exterior of the home is characterized by a light brown facade with dark shutters framing two large windows. A welcoming entrance is highlighted by a gray step leading to the front door, situated under a small overhang.

4.97 out of 5 average rating, 282 reviews

Redmond Downtown Retreat

The exterior of the home displays a combination of dark blue siding and natural stone accents. A spacious front porch is featured, along with two garage doors and a wide paved driveway. The sloped roof adds to the home's structural interest.

4.85 out of 5 average rating, 115 reviews

Stunning mtn Views, sleeps 14, Hot tub, rec passes

Other great vacation rentals in Redmond

4.86 out of 5 average rating, 214 reviews

Guest suite in Redmond

Light & bright, private guest suite with hot tub!

Cabin in Crooked River Ranch

A row of rustic cabins is set against a natural backdrop, showcasing wooden exteriors and inviting porches. Each cabin features a distinct entrance, with picnic tables arranged on the deck. A gravel path leads through the surrounding shrubbery, offering a sense of tranquility.

4.93 out of 5 average rating, 122 reviews

Classic Cozy Cabin with Awe-inspiring Views

5 out of 5 average rating, 103 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

4.88 out of 5 average rating, 283 reviews

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.

Townhouse in Redmond

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

4.9 out of 5 average rating, 284 reviews

A side view of the guesthouse is showcased, featuring a blue exterior and a fenced area. Planters with fresh greenery are positioned along the pathway, which is lined with mulch, enhancing the outdoor space. A grassy area is visible in the background.

Guesthouse in Terrebonne

Compound Coziness...Terrebonne Guesthouse

4.93 out of 5 average rating, 41 reviews

A modern kitchen is presented with sleek cabinetry in earthy tones. A spacious island is equipped with bar stools and features a cooktop. Overhead lighting provides illumination, while a vase of white flowers enhances the countertop's simple elegance.

Guesthouse in Redmond

Brand New Downtown Redmond Private ADU on Canyon

4.98 out of 5 average rating, 260 reviews

The exterior of the chalet is showcased, featuring a peaked roof and large windows that allow ample natural light. A spacious wooden deck is present, accompanied by outdoor seating and a barbecue. The surrounding grassy area enhances the outdoor setting.

Chalet in Eagle Crest

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!