Holiday rentals with a kayak in Deschutes River

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Top-rated Accommodation with a Kayak in Deschutes River

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Guest favourite

The living room features a stone fireplace surrounded by wooden shelves, with a large flat-screen TV mounted above. A rustic wooden coffee table sits on a patterned area rug, complemented by leather seating and large windows that allow natural light to flood the space.

Home in Bend

4.96 out of 5 average rating, 133 reviews

Sunriver Luxury Family Home at Caldera Springs

Your next adventure begins here! Explore the limitless activities of Central Oregon from our luxurious home in Caldera Springs Resort at Sunriver located 14 miles South of Bend. Built for families and friends with three bedroom suites, upstairs loft bedroom with bunk beds & sofa bed, and flexible office with sofa bed. Features private hot tub, outdoor gas fire pit and BBQ, game room with ping pong/foosball/arcade, big screen TVs, Sonos, and more! Short walk to Caldera Springs pool and amenities.

Top Guest favourite

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

5 out of 5 average rating, 124 reviews

River Run Bend Bungalow & Romantic Spa Grotto

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally-located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding and pillows, dedicated free parking (incl. extra cars or small RV), outdoor dining and patio area, washer/dryer, and kitchen fully stocked with everything you need for fun and relaxation for all seasons!

Guest favourite

A cozy bedroom features a log bed with decorative pillows, complemented by a ceiling fan. Natural light filters through a large window, illuminating warm wooden flooring. An accent lamp and a small plant are placed beside the bed, adding subtle elements of design.

Guest suite in Bend

4.93 out of 5 average rating, 296 reviews

Cozy Queen, Private Bathroom and Entryway

Peaceful, intimate bedroom (referred to as a “studio”) with a generously sized bathroom. Facing a large, sunny community space, enjoy amenities like a Keurig, heated bathroom floors, log bed, AC and PRIVACY. Experience a quaint, welcoming atmosphere, making it effortless for you to focus on what truly matters—creating cherished memories during your stay. This studio features WiFi, washer/dryer, kitchen essentials, TV with streaming, EV charger and self-check in. The studio is 300 square feet.

Top Guest favourite

A spacious backyard is shown, featuring a well-manicured lawn and a shaded seating area. The modern chalet is visible in the background, with large windows and a stone chimney. A hot tub is positioned nearby, integrating relaxation into the outdoor space.

Chalet in Bend

4.94 out of 5 average rating, 137 reviews

Chalet del Sol - Hot Tub - Ping Pong - Fire pit

Welcome to the cozy Chalet del Sol just South of Old Mill District and close to the hiking trails. What this home offers: ☞ Entire property to yourself ☞ Hot tub ☞ BBQ & Blackstone ☞ Ping Pong Table ☞ Master w/king bed upstairs ☞2nd bedroom downstairs queen bed ☞3rd bedroom is a loft w/queen & 2 twins ☞Two full bathrooms ☞ Fast WIFI ☞ Garage ☞ Fully equipped chef’s kitchen ☞ 65” Smart TV w/ Netflix ☞ Lots of Parking → 4 plus cars ☞ Private yard ☞ Washer + dryer ☞ Ductless heating and cooling

Guest favourite

A spacious studio apartment is shown, featuring a combination of cozy seating and a dining area. Natural light fills the room through glass doors that lead outside. A bed is visible in the background, creating a functional and inviting living space.

Guest suite in Sunriver

4.92 out of 5 average rating, 615 reviews

Pepper’s Place

Private marina & hot tub — cozy studio Apt with no shared walls. 7-min drive to the Village at Sunriver via S. Century, 20 mins to Bend, 25 minutes to Mt. Bachelor. SUPs (2), kayaks (2), floats, rafts, and bikes (2 adult + 2 kid), snowshoes (4 pairs). Pepper is a friendly golden/boxer mix who loves kids and dogs. Pet friendly (no fee), fenced yard, hot tub, propane and wood fire pits, OWW. Sound-deadened movie theater and foosball room available upon request. Backyard is shared with Pepper.

Guest favourite

The modern A-frame cabin is surrounded by snow-covered trees, highlighting its dark exterior. A deck extends around the cabin, accentuated by a row of small evergreen planters against the backdrop of a winter landscape, showcasing the serene setting.

Cabin in Sisters

4.92 out of 5 average rating, 129 reviews

Popular BBR A-Frame | 2 golf courses | 5 pools

Welcome to Your Modern A-Frame Cabin at Black Butte Ranch! - Accommodations: Sleeps 8 in 2 queen bedrooms and a 2 twin loft, and trundle downstairs - Amenities: Relax in the living area with a Roku TV; the chef's kitchen makes meal prep easy, and self check-in ensures a smooth arrival - Sunny Recreation: Access to 6 pools, including the nearby Paulina pool, plus golf, pickleball, horseback riding, and hiking - Winter Fun: 20m drive to HooDoo Ski Resort Book your unforgettable getaway today!

Guest favourite

An A-frame cabin is set against a colorful sunset, showcasing warm lights illuminating the exterior. The front entrance features a door with a welcoming window, while two rustic chairs sit on the porch, accompanied by potted plants and neatly stacked firewood.

Cabin in Bend

4.93 out of 5 average rating, 226 reviews

Black Duck Cabin

Cozy A frame cabin set in a quiet neighborhood among the pine trees just a short walk from the Deschutes River. The Black Duck Cabin is a perfect destination for all of Central Oregon's amazing activities. 10 minute drive to Sunriver Village, 30 minute drive to Mt. Bachelor, 30 minutes to Downtown Bend, 10 minute walk to the Deschutes River, golfing, fishing, hiking, shopping, mountain biking, all a short drive. If you're looking for a rustic, cabin experience this is the place for you!

Guest favourite

The exterior of a two-story house is showcased, featuring a mix of dark green and beige siding. A spacious wooden deck is adorned with multiple outdoor seating options, including loungers and a hammock. Tall trees surround the property, contributing to a serene natural setting.

Home in Bend

4.92 out of 5 average rating, 105 reviews

Riverfront Cabin

This cozy retreat offers the perfect blend of comfort and natural beauty, making it an ideal getaway for families and friends. Nestled on the banks of the Deschutes River, this rental house offers breathtaking views and a serene atmosphere. With two bedrooms, a sleeping loft, and two bathrooms, it comfortably accommodates eight guests who desire a peaceful escape. The home provides comfortable beds, local photography, a hot tub, SUPs and kayaks, games for endless family fun.

Guest favourite

A gravel driveway leads to a single-story home nestled among tall pine trees. The house features a neutral exterior and is set back from the road, surrounded by a grassy area, offering a sense of privacy in a tranquil setting.

Home in Bend

4.87 out of 5 average rating, 125 reviews

Wooded river retreat near Sun River & Bend

Enjoy skiing, hiking, fishing, kayaking (2 provided) -- you name it -- from our peaceful Deschutes River 3-bedroom home. Inside: -Cozy living room -- w/pull-out bed & TV (fiber WiFi) -Kitchen & table which seats up to 8 (w/extensions) -3 bedrooms: Master, room w/queen, & room w/2 twins Outside: -Porch w/rocking chairs & table -Back patio w/table & BBQ -River 5 min, marina 15 min walk Location: -5 min Sun River -20 min Bend -30 min Mt. Bachelor *Dogs welcome: $75 per dog

Guest favourite

A private hot tub bubbles gently in a secluded outdoor space, surrounded by wood-paneled walls and evergreen trees. Two towels hang on a nearby railing, and small potted plants adorn the fence, adding a touch of greenery to the serene setting.

Home in Bend

4.85 out of 5 average rating, 130 reviews

Sunriver Area Retreat + EV Charger + Hot Tub!

Welcome to your next amazing getaway! Our house is SOUTH of Sunriver proper, about 10 minutes away and we don’t have SHARC passes. But.. from our front door, enjoy all that Central Oregon has to offer at our family and dog-friendly home! Located just one block (3 minute walk) from the Deschutes River, private community pool, tennis and pickle-ball courts or stay home and relax in the private hot tub. Our place is a perfect active family getaway.

Top Guest favourite

A snowy slope is visible leading down to a cozy two-story Barndominium, surrounded by tall pine trees. Warm lights illuminate the exterior, creating a welcoming ambiance. A figure is seen sledding down the hill, showcasing a fun winter activity right outside the home.

Home in Crescent

4.99 out of 5 average rating, 128 reviews

Crescent Butte Barndominium with Disc Golf

Take advantage of low Spring prices! Our 2 bed, 2 bath Bardominium is filled with extras including a sledding hill, snowshoeing on the property, private 9 hole disc golf course and a Level 2 EV Charger. Enjoy the view of Diamond Peak, hiking in the Gilchrist State Forest right out the door. We are about 45 miles to the N. entrance of Crater Lake. The "Barn" is perfect for 2 couples, or families. Enjoy this upscale country setting.

Guest favourite

A comfortable living area features a green sectional sofa and a gray accent chair. A large coffee table sits in the center, with a light-colored rug beneath. Exposed wooden beams adorn the ceiling, while a staircase leads to an upper level. A television is mounted on the wall.

Home in Bend

4.93 out of 5 average rating, 196 reviews

Drake Park Cottage in the Heart of Bend

This location can’t be beat! The cottage is steps away from Drake Park and the river as well as walking distance to downtown. Enjoy summer festivals in the park, floating or stand up paddleboard on the river. Located in the historic parks district, this property is quiet and comfortable yet close to all the action. Guests have been coming back year after year to enjoy this unique vacation spot. It’s a gem! SORRY NO PETS and NO SMOKING.