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.

4.97 out of 5 average rating, 129 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, 164 reviews

A round cabin is surrounded by tall trees, with a wide deck wrapping around its exterior. The deck features seating areas, while large windows allow views of the interior. The landscape is covered in pine needles, enhancing the natural setting.

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, 109 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!

The cabin's exterior is crafted with natural wood and features large, angular windows that showcase the surrounding forest. A spacious deck with Adirondack chairs extends across the front, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 167 reviews

Private Luxury w/Hot Tub on Pvt Lake Amazing Views

The private & spectacular Lakeside West Cabin (3 bedr/3.5 bath, sleeps 8) overlooks Tumalo Lake with cozy wood-burning stove, private hot tub, & amazing lake views. 12 mi to downtown Bend, 45 min to Mt Bachelor and 4 mi to Tumalo Falls. Immerse in nature and be as active as you choose: hiking, mountain biking, fishing, complimentary canoes, kayaks, SUPs, snowshoeing, sledding, hammock, horseshoe and corn hole game, shared fire pit. Need more or less space? We have 2, 4 and 6 - 8 bedroom cabins.

4.93 out of 5 average rating, 290 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, 130 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, 123 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!

The cabin's exterior features a combination of wood and large glass panels, creating a warm and inviting entryway. Surrounded by tall pine trees, the snowy landscape enhances the sense of tranquility. A front porch with steps leads to the main entrance.

4.91 out of 5 average rating, 147 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, 221 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!

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.

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.

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, 127 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, 192 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.

Popular amenities for Bend kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A cozy living area features light-colored walls and a large window providing natural light, framed by blue curtains. A fireplace is situated beneath a wall-mounted television. A wooden coffee table sits centrally, adorned with brochures. Comfortable sofas are arranged around the space.

4.95 out of 5 average rating, 126 reviews

Large Black Bear Cabin in Three Rivers w/ wildlife

The exterior of a charming two-story home is surrounded by tall trees, featuring a welcoming porch with seating. A neatly arranged driveway provides access to a garage, and flower pots line the entrance. Sunlight filters through the branches, creating a serene atmosphere.

4.95 out of 5 average rating, 111 reviews

Deschutes River Getaway-near Bachelor & Sunriver

A charming outdoor space is featured, characterized by a gravel pathway bordered by greenery and plants. A wooden bench is positioned nearby, providing a peaceful spot to enjoy the natural surroundings. The property is enveloped by tall trees, enhancing the tranquil atmosphere.

5 out of 5 average rating, 9 reviews

Ponderosa Pine Oasis on 1 acre in BEND

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.

4.87 out of 5 average rating, 123 reviews

Wooded river retreat near Sun River & Bend

A comfortable living area features a sectional sofa and leather ottoman, surrounded by stylish armchairs. Large windows provide views of the surrounding trees, while natural light enhances the space. A neutral color palette is complemented by decorative pillows and a wall art piece depicting a bike.

4.87 out of 5 average rating, 159 reviews

Pet-Friendly Riverfront Home w/ Deck

The outdoor area is surrounded by lush green grass, featuring a fire pit at the center with several blue Adirondack chairs arranged around it. A hot tub is positioned nearby, with a spacious house in the background, framed by tall pine trees.

4.99 out of 5 average rating, 187 reviews

Treehouse Retreat • Hot Tub • Game Room •River Fun

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, 6 reviews

New! Brand New Furniture~Close to Trails~Fireplace

The living area features a large sectional couch positioned around a central wagon wheel coffee table. A gas fireplace is set within a stone surround, and a 65” smart TV is mounted on the wall. Natural light fills the space through multiple windows.

4.94 out of 5 average rating, 66 reviews

New 3BR Close to Village! Hot Tub SHARC Pets WFH

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.

4.95 out of 5 average rating, 63 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, AC & Views

4.95 out of 5 average rating, 40 reviews

A-frame w/ hot tub near Mt. Bachelor

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

A handcrafted log cabin showcases a spacious two-story structure surrounded by snow-covered trees. The exterior features large windows and a welcoming balcony, while a garage is visible to the left. The serene winter landscape highlights the cabin's rustic charm.

4.9 out of 5 average rating, 108 reviews

Rustic Retreat Handcrafted Log Cabin

The cabin's exterior features a welcoming entrance with wooden steps leading to a modern door under a spacious, covered porch. Surrounded by tall pine trees, the natural landscape is complemented by stone pathways and a gently sloping yard.

Cabin in Sisters

Black Butte Ranch Ridge Cabin 010

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.

4.98 out of 5 average rating, 47 reviews

Sunriver/Bachelor *RiverFront* Cabin

Other vacation rentals with a kayak

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

4.97 out of 5 average rating, 58 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

A cozy living area features light wood paneling and large windows. A comfortable sectional sofa, accented with orange and gray pillows, is positioned on a plush area rug. A wood stove adds warmth, while a framed landscape artwork complements the natural tones.

Condo in Sisters

4.78 out of 5 average rating, 144 reviews

Country House Condo with a View

Bungalow in Bend

New place to stay

Riverfront Retreat near Bend's Drake Park

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

5 out of 5 average rating, 7 reviews

Guesthouse in Bend

Peaceful Hobby Farm, Gateway to Outdoor Adventure