Vacation rentals with a kayak in Bend

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.

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.

4.98 out of 5 average rating, 165 reviews

A wooden dock extends over the clear waters of the Spring River, featuring a bright yellow kayak resting on the edge. A paddle lies nearby, and lush greenery surrounds the tranquil scene, providing a serene backdrop of trees and natural beauty.

Cabin in Sunriver

Riverfront Ski Cabin w/ HotTub & Dock

Riverfront cabin w/ fantastic location! Conveniently located to the Sunriver Village (5 min) & Mt. Bachelor (20 min). Take it easy @ this unique, round house perched over the Spring River w/ 2 levels of decking, hot tub & private dock! Enjoy snow activities, hiking & biking. Kayaks, SUP, canoe & bikes available during summer.Stunning 180 degree views of the river. House is well stocked w/ all the creature comforts. This home is truly a peaceful oasis for some fun and R&R! 1 dog limit, $100 fee.

5 out of 5 average rating, 124 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

**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!

4.88 out of 5 average rating, 383 reviews

Adventure Retreat - Sunriver/Bachelor/Waterfront

Our home is special for its location providing easy summer access to water on the Deschutes River and easy winter access to snowy adventures on Mt Bachelor. Summer months are booked early by guests who love our peaceful water views and access to their private dock, kayaks & bicycles. Our winter months welcome guests looking to experience snowy pines and easy access to Mt Bachelor's powdery slopes and surrounding trails. Summer or winter guests celebrate our pristine hot tub, morning to evening.

4.93 out of 5 average rating, 297 reviews

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

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.

4.94 out of 5 average rating, 137 reviews

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

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

4.98 out of 5 average rating, 125 reviews

Lush green grass extends beneath tall trees along the riverbank, with soft shadows created by the sunlight filtering through the branches. Several ducks are seen gracefully walking on the vibrant lawn, contributing to the tranquil natural setting.

Home in River West

Riverfront Lodge

The house sits on an acre of land right on the Deschutes river with over 200 ft of frontage. With private dock, kayaks, canoes and a row boat, you can enjoy the river and the wonderful view. Two large decks with furniture and fire pit are great for outdoor BBQ's and just watching the wildlife. Otters, beaver, deer, ducks, geese and swans make the back yard their home. There are 6 bikes, river tubes and a ping pong table in the garage. Come and enjoy, I guarantee you will want to come back!

4.92 out of 5 average rating, 153 reviews

Sunriver cabin near Mt. Bachelor

Come enjoy a get-away in Sunriver where you can relax and unwind or explore all that Central Oregon has to offer. The Cabin on Cooper is ideally located only minutes away from the Deschutes River, golf courses, shopping, Mt. Bachelor, and the Cascade Lakes making it the perfect retreat for large groups, corporate events, and families. When you return from your adventures, enjoy the hot tub and cozy atmosphere, or get competitive with a game of wiffle ball or miniature golf in the backyard.

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.

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!

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.

4.85 out of 5 average rating, 131 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.

4.93 out of 5 average rating, 196 reviews

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 Old Bend

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.

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.

4.96 out of 5 average rating, 176 reviews

Best for Old Mill:River Trail, Views & Town

Awesome location! Fast internet, Wi-Fi. Clean and close to everything that is great in Bend - the river, Mt. Bachelor, restaurants, nightlife, cycling, kayaking, paddle boarding, hiking, breweries, concerts and so much more. You’ll love the location, ambiance, the outdoor space, and the comfy bed. Walk along the river trail to experience what everyone loves about Bend. Easy drive to Mt. Bachelor, approximately 25 minutes.

Popular amenities for Bend kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The exterior of the home features a modern architectural design with large glass panels reflecting the surrounding trees. A spacious wooden deck extends from the structure, providing a seamless transition to the natural landscape. Sunlight filters through the pine trees, creating a serene atmosphere.

5 out of 5 average rating, 22 reviews

Black Chair Inn

4.95 out of 5 average rating, 59 reviews

Large windows dominate the walls of this inviting living space, offering views of the surrounding forest. Two leather couches and a wooden coffee table are arranged on plush carpeting, complemented by a comfortable armchair and wooden chairs, creating a cozy gathering area.

Home in Sunriver

5 out of 5 average rating, 56 reviews

The spacious living room features vaulted wood ceilings and large floor-to-ceiling windows, allowing natural light to fill the area. Comfortable seating arrangements include a sectional sofa, recliners, and a coffee table. A gas fireplace is positioned against the wall, enhancing the inviting ambiance.

Home in Sunriver

⁂ Grand Getaway | Chef's Kitchen | +SHARC passes ⁂

4.95 out of 5 average rating, 19 reviews

Deschutes River Front Home

A single-story home is surrounded by greenery, featuring a well-maintained lawn and a gravel pathway. A wooden bench is positioned on the front porch, and large windows provide views into the interior. The structure showcases a sloped roof and a welcoming entrance.

4.91 out of 5 average rating, 95 reviews

Entire Sunriver House, SHARC Passes

The exterior of the Cedar Retreat is shown, featuring a wood paneling structure with a welcoming sign. A spacious deck is furnished with a dining set and an umbrella. A charcoal grill is positioned nearby, surrounded by lush greenery.

5 out of 5 average rating, 7 reviews

Cedar Retreat Waterfront, Spa 4Bed

The exterior of the single-level home is framed by tall pine trees, providing a natural setting. A covered front porch with seating is visible, inviting relaxation. The garage and pathway are shown along with the structured roofline, reflecting a cozy, welcoming ambiance.

4.95 out of 5 average rating, 20 reviews

13 Stag Lane, Sunriver

A spacious living area features a stone fireplace, providing warmth and comfort. Large windows allow natural light to illuminate the room, showcasing wooden accents and a colorful area rug. A flat-screen television is mounted above the fireplace, complementing the inviting decor.

5 out of 5 average rating, 8 reviews

New! Brand New Furniture~Close to Trails~Fireplace

Cabin rentals with a kayak

A charming A-frame cabin is surrounded by tall pine trees, featuring a spacious front porch with two rocking chairs and a set of steps leading to the entrance. Large windows allow natural light to fill the interior, enhancing the welcoming atmosphere.

4.96 out of 5 average rating, 68 reviews

Riverwoods A-Frame

An outdoor fire pit is surrounded by several chairs, offering a cozy gathering spot. Behind it, a two-story cabin is visible, featuring large windows and a spacious deck. Soft evening light casts a warm glow on the wooden surfaces, creating a welcoming atmosphere.

4.88 out of 5 average rating, 16 reviews

Riverfront Cabin w/ Trails, Hot Tub, Wood Stove, A

4.95 out of 5 average rating, 42 reviews

A-frame w/ hot tub near Mt. Bachelor

A luxury cabin is presented with a wooden exterior and a peaked roof, surrounded by tall trees. Illuminated windows create a warm glow, highlighting the expansive wrap-around deck equipped with chairs. The structure integrates natural materials, blending seamlessly into the forest environment.

4.93 out of 5 average rating, 107 reviews

Romantic Luxury w/Hot Tub, Amazing Lake Views

An A-frame cabin is showcased with a wooden deck and a sloped roof. Large windows allow natural light to enter, surrounded by tall pine trees. The front door is centrally positioned, adding charm to the home's exterior.

Cabin in La Pine

4.66 out of 5 average rating, 87 reviews

Tall Pines Guest House comes with rental canoe

The cozy living room features a large sectional sofa alongside a full sleeper sofa, both positioned around a rustic wooden coffee table. A vibrant area rug complements the warm cabin decor, with natural light streaming through the window and a wooden sliding door visible in the background.

Cabin in La Pine

4.37 out of 5 average rating, 27 reviews

Private La Pine Cabin Rental: 30 Mi to Bend!

A serene view of the river reflects surrounding trees and cabins, with wooden docks leading into the calm water. The soft morning light highlights the greenery along the banks. A kayak is seen gliding across the water, adding to the peaceful ambiance.

4.96 out of 5 average rating, 48 reviews

Sunriver/Bachelor *RiverFront* Cabin

4.86 out of 5 average rating, 35 reviews

Custom Built Log Cabin Deschutes River, floating

Other vacation rentals with a kayak

An aerial view captures the Pony Express River Retreat nestled among tall pines with the Upper Deschutes River winding nearby. The spacious property, highlighted with an arrow, shows its proximity to lush greenery and water, emphasizing a serene natural setting.

4.94 out of 5 average rating, 31 reviews

Pony Express River/Mountain Retreat

New place to stay

Exclusive Riverfront Estate - 1.5 acres

An outdoor deck area is shown, featuring a spacious seating arrangement with blue cushions and multiple lounge chairs. A brown dining table is positioned under an orange umbrella, providing shade. Surrounding trees add a natural backdrop, enhancing the overall ambiance.

4.96 out of 5 average rating, 55 reviews

Perfectly located getaway! Walk to the river!

The exterior view showcases a charming multi-unit building surrounded by landscaped gardens. Pathways lead to the entrance, lined with natural stone and flower beds, emphasizing the tranquil ambiance. Lush trees provide shade, and the blue sky enhances the peaceful setting.

Condo in Bend

WorldMark Bend Seventh Mountain Resort - 1BD Sleep

A wooden structure with a metal roof is positioned near a serene riverbank. Tall pine trees frame the scene, casting gentle shadows. A small deck with seating overlooks the calm water, while the surrounding landscape features grass and distant hills under a clear blue sky.

Condo in Bend

Otterspot on the Deschutes River w/Hot Tub

4.83 out of 5 average rating, 12 reviews

Home in Sunriver

SHARC 8 A/C Bikes Kayaks Tubes BBQ Village

4.95 out of 5 average rating, 42 reviews

The open living space features wooden beams and a cozy wood-burning stove. The staircase leads to a sleeping loft above. A flat-screen TV is mounted on the wall, while light streams in through large windows overlooking the property. A dining area is visible in the background.

Guesthouse in La Pine

Guesthouse Retreat w/ friendly horse neighbors!