Vacation rentals in Redmond

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Top-rated vacation rentals in Redmond

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Guest favorite
A spacious deck is framed by a wooden pergola, featuring two individual chairs positioned for relaxation. Wide windows of the cottage allow natural light to fill the space, while the surrounding landscape reveals expansive views of native plants and shrubs, enhancing the overall tranquility.
Cottage in Terrebonne
4.9 out of 5 average rating, 327 reviews

Quiet central Oregon desert retreat with a view!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

Top guest favorite
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, 673 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.

Guest favorite
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.
Home in Redmond
4.86 out of 5 average rating, 119 reviews

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

Enter the first floor to immediate views of the Cascade Mountain range. The fully-equipped kitchen with Sub-Zero Fridge and gourmet range has direct access to the wrap-around deck, which features an outdoor dining area gas fireplace & gas grill. Upstairs you’ll find the primary suite with king bed with a private balcony boasting views of seven Oregon’s tallest peaks; the bunk room, & queen bedroom. Downstairs is another bedroom, game room, wet bar, 65” TV, & access to the hot tub. Don’t wait!

Guest favorite
A bright great room features large windows that invite natural light and views of the surrounding greenery. A gas fireplace is situated beneath a framed artwork. Comfortable seating includes a sectional sofa and armchairs, complemented by a coffee table adorned with decorative plants.
Townhouse in Redmond
4.91 out of 5 average rating, 141 reviews

Quiet Eagle Crest Townhouse w/ Access to Amenities

Enjoy all that Central OR has to offer in this quiet, end-unit townhouse. Located in Eagle Crest Resort, a 1700-acre resort with one spa, three sports centers, five pools, and three full year-round golf courses, it is the ideal location to enjoy Central OR. This 1400sq ft single-level townhome features a great room with soaring ceilings, walls of windows, a fully stocked kitchen, and plenty of gathering spaces. Perfect for a romantic getaway, fun family weekend, or adventure-filled vacation.

Top guest favorite
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.
Home in Terrebonne
4.98 out of 5 average rating, 272 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

Top guest favorite
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
4.97 out of 5 average rating, 551 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 favorite
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
4.97 out of 5 average rating, 352 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 favorite
A private patio area is showcased under a pergola, featuring a small table with two chairs. Vibrant flowers and greenery surround the space, enhancing the tranquil environment. Sunlight casts gentle shadows across the concrete floor, creating an inviting spot for relaxation.
Guest suite in Redmond
4.99 out of 5 average rating, 201 reviews

Momma Sal's Studio in Downtown Redmond

Charming, beautiful studio w private entrance, patio, amazing stone fireplace (gas), coffee maker, mini fridge, microwave, glassware, dishes, very nice linens & bath. Downtown, quiet neighborhood. Easy walk to restaurants, shops, great craft brews, events. Dry Canyon few blocks away for disc golf, walking, running, biking, hiking trails. Lovely parks. Close to Expo, 20-30 min to Bend, Smith Rock, Sisters, Prineville. Great C.O. location in every direction for fun & recreation all seasons.

Top guest favorite
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, 344 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.

Guest favorite
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.
Guesthouse in Bend
4.98 out of 5 average rating, 425 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 favorite
A plush, tufted brown sofa is placed in a refined living area, complemented by two decorative cushions. An ornate mirror hangs above, reflecting the warm hues of the space. Nearby, a glass cabinet displays decorative items, and a potted plant adds a touch of greenery.
Apartment in Larkspur
4.96 out of 5 average rating, 127 reviews

The French Farmhouse at Midtown Manor - Hot Tub!

Step into a world of opulence and elegance at the French Farmhouse, the epitome of French provincial style. The main floor of a charming 3-floor home, this retreat offers a luxurious and comfortable escape. Adorned with lavish furnishings and exquisite details including a master suite, full kitchen, with its blend of modern amenities and vintage charm, a large TV for nights in, and a private patio beckons with hot tub. Close to local attractions, a memorable stay filled awaits you.

Top guest favorite
The exterior of a modest studio is showcased, featuring light grey siding and a black front door. Windows with white trim let in natural light. A small set of steps leads up to the entrance, with well-maintained greenery including pink flowers and shrubs framing the pathway.
Apartment in Redmond
4.99 out of 5 average rating, 301 reviews

Redmond Retreat - stylish studio with full kitchen

Quiet, upscale studio conveniently located in the hub city of Redmond, 3.5 miles to the airport, 7 to Smith Rock, 14 to Bend and 18 to Sisters. Close to restaurants and grocery shopping. Spotlessly clean, with all the personal touches you expect and amenities perfect for two. Fully equipped kitchen, table for meals or work space, Big-screen smart tv (Direct TV service), 5G WiFi, AC. Private parking, direct laundry access. We cannot accommodate pets.

Popular amenities for Redmond vacation rentals

When is the best time to visit Redmond?

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Frequently Asked Questions

  • What are the best places to stay in Redmond?

    Redmond has welcoming neighborhoods and plenty of vacation rentals near local parks, downtown shops, and family-friendly attractions. Consider staying around the historic downtown area to easily explore dining, events, and outdoor spaces.

  • What are the best things to do in Redmond with kids?

    Families often explore community parks, splash pads, and interactive museums, or enjoy outdoor activities at nearby nature areas. The region has play spaces and seasonal events that are frequently suggested for children.

  • What are some of the best things to do in Redmond?

    Redmond has scenic parks, river trails, boutique shops in the historic downtown, and nearby lava caves for those interested in geology. Visitors frequently enjoy local breweries, walkways, and art installations.

  • How is the weather in Redmond?

    Redmond experiences dry, sunny summers with afternoons near 88°F (31°C), and winters around 23–44°F (-5–7°C) with occasional snowfall. Light rainfall is typical, so layers and sturdy shoes make exploring comfortable year-round.

  • When is the best time to visit Redmond?

    Summer and early fall are often recommended for warm weather, festivals, and outdoor adventures. In spring, blooming wildflowers and milder temperatures draw visitors to trails and public spaces.

  • What are the best places to visit in Redmond?

    Explore the historic downtown, stroll through city parks, and learn about local history at the nearby museum. Lava tube caves and public art also draw visitors seeking unique experiences.

  • What are some hiking trails in Redmond?

    Redmond has riverfront paths, forested trails, and scenic routes through volcanic landscapes. Community parks and nature preserves frequently provide easy-to-access hiking opportunities for various experience levels.

  • What are some family activities we can do in Redmond?

    Enjoy playgrounds, local splash pads, interactive museum exhibits, and outdoor picnics at city parks. Seasonal festivals and family-focused events are frequently suggested for visitors with children.

  • What are some of the best day trip ideas from Redmond?

    Visitors often plan trips to explore the Cascade Mountains, volcanic parks, and scenic lakes near Redmond. Day excursions to neighboring towns with art galleries, outdoor markets, and historic sites are also popular.

  • Are there any pet friendly accommodations available in Redmond?

    Many vacation rentals in Redmond welcome pets, especially in neighborhoods near public parks and walking trails. Check individual listings for pet policies and amenities suited to your companion.

  • What are some local tips for visiting Redmond?

    Wear layers, as weather shifts between dry heat and cool evenings, and sturdy shoes are helpful for exploring rough terrain or lava caves. Locals often recommend checking community calendars for events and farmer’s markets.

  • What is Redmond known for?

    Redmond is known for its high desert landscape, river access, and proximity to volcanic formations. The city enjoys a blend of outdoor recreation, community events, and local craft culture.

  • What are the best hidden gems to explore in Redmond?

    Redmond has small art studios, locally owned cafes, and lesser-known trails winding through unique geological features. Quiet parks and community gardens also invite visitors to relax or explore off the main paths.

  • What are the best foods to try in Redmond?

    Redmond has locally raised beef, fresh produce, and craft brews, reflecting Central Oregon's agricultural roots. Huckleberry treats, ranch-inspired plates, and hearty breakfasts featuring local ingredients are often recommended by visitors and residents.

  • What should I bring for a trip to Redmond?

    Pack layers, sunscreen, a hat for sun protection, and sturdy shoes for exploring trails or volcanic areas. A reusable water bottle, jacket for cool evenings, and outdoor gear add comfort to your visit.

  • What is the nightlife in Redmond like?

    Redmond’s nightlife centers around casual pubs, live music venues, and local breweries. The historic downtown has gathering spots for food, drinks, and occasional performances in an inviting atmosphere.

  • What are the most popular events or festivals in Redmond?

    Redmond hosts a summer rodeo, seasonal craft fairs, and community celebrations during holidays like the Fourth of July. Local music festivals and park events are also frequently suggested throughout the warmer months.

  • Are there family friendly vacation rentals in Redmond?

    Redmond has many family-friendly vacation rentals, including homes near parks, splash pads, and attractions. These stays often provide amenities like play spaces and extra bedrooms for group comfort.

Quick stats about vacation rentals in Redmond

  • Total vacation rentals

    Explore 190 vacation rentals in Redmond

  • Nightly prices starting at

    Redmond vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 13,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Redmond vacation rentals include wi-fi 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!

  1. Airbnb
  2. United States
  3. Oregon
  4. Deschutes County
  5. Redmond