Holiday rentals in Redmond

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Top-rated holiday rentals in Redmond

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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.
Guest house in Terrebonne
4.87 out of 5 average rating, 278 reviews

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.

Guest favourite
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.
Home in Redmond
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.

Top guest favourite
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.
Flat in Redmond
4.97 out of 5 average rating, 543 reviews

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

Top guest favourite
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
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.

Top guest favourite
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.
Home in Terrebonne
4.99 out of 5 average rating, 309 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.

Top guest favourite
A spacious living area features two comfortable sofas adorned with colorful decorative pillows. A coffee table sits in the center, and a large bed is positioned in the background, draped in a bright quilt. Natural light floods through large windows, illuminating the open space.
Guest house in Bend
4.98 out of 5 average rating, 424 reviews

Bend Ranch Guesthouse on 20 acres

Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.

Top guest favourite
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.
Flat in Redmond
4.98 out of 5 average rating, 208 reviews

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"

Top guest favourite
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.
Home in Redmond
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...

Guest favourite
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.
Home in Redmond
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.

Guest favourite
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
4.89 out of 5 average rating, 228 reviews

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.

Guest favourite
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.
Home in Redmond
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.

Popular amenities for Redmond holiday rentals

When is the best time to visit Redmond?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Redmond?

    Four-legged friends are welcome in Redmond. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Redmond?

    Yes! Work meets play with ease at over 90 vacation rentals in Redmond featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Redmond?

    Redmond has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do private suite rentals in Redmond have air conditioning?

    Absolutely! We offer over 10 private suite rentals with air conditioning in Redmond. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in private suite rentals in Redmond?

    Experience the best of Redmond with our private suite rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Redmond have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Redmond. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Redmond have wifi?

    Absolutely! We offer over 10 private suite rentals with wifi in Redmond. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Redmond?

    Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with air conditioning, over 120 homes with wifi, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Redmond

  • Total holiday rentals

    Explore 190 holiday rentals in Redmond

  • Verified guest reviews

    Over 13,150 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    190 of Redmond holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Redmond rentals

  • 4.9 Average rating

    Redmond stays are highly rated by guests – averaging 4.9 out of 5!

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  3. Oregon
  4. Deschutes County
  5. Redmond