Holiday rentals with a kayak in Bend

4.98 out of 5 average rating, 162 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.

4.99 out of 5 average rating, 201 reviews

An aerial view captures the expansive property featuring a lush English Country Garden filled with vibrant flowers and greenery. A serene swimming pond is visible in the foreground, while the well-maintained guest suite is framed by trees in the background.

Guest suite in Bend

Luxurious Private Tumalo Suite Nestled in Trees

The Treehouse Guest Suite is nestled in the trees in the beautiful community of Tumalo, Oregon! Tumalo, a short 10 minute drive west of Bend, is well known for its beauty to include easy access to hiking and biking trails. Your second floor craftsman style guest suite is surrounded by trees and includes a private entrance, garage, and deck. Our farm has scenic views of the Cascade Mountains. During the summer, guests can enjoy our English Country Garden, swimming pond, and Alpacas in the field.

4.93 out of 5 average rating, 281 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.

A private outdoor deck features a hot tub positioned near the water's edge. Surrounded by tall trees, the area offers scenic views of the river and surrounding wetlands. Comfortable seating is available nearby for relaxation.

4.91 out of 5 average rating, 142 reviews

Big River Getaway *Spectacular Riverfront Property

DCCA #742522 Magical location w/ over 100 ft of frontage on the Deschutes River. This 2-story, classic NW contemporary 3 bedroom, 2 bathroom home is an outdoor enthusiast's dream. Relax in the hot tub located 40 feet from the water's edge with spectacular panoramic views of the river and natural wetlands. The house is complete with a canoe, two-man kayak, and tubes for enjoying the beautiful Deschutes from your private boat ramp. Conveniently located just 8 mins from the amenities of Sunriver.

4.93 out of 5 average rating, 121 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

4.99 out of 5 average rating, 122 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 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, 182 reviews

Treehouse Escape • Hot Tub • Game Room • River Fun

Your Ultimate Bend Family Retreat Welcome to Treehouse Escape, a spacious Bend getaway for up to 15 guests. Kids will adore the private treehouse, swings, and slides, while adults relax in the hot tub or gather around the fire pit. With a full game room, chef’s kitchen, and outdoor dining under the pines, this pet-friendly retreat blends adventure and comfort for an unforgettable family escape. Minutes from the Deschutes River, Sunriver Village, and Mt. Bachelor, it’s perfect for all ages.

4.92 out of 5 average rating, 595 reviews

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

Pepper’s Place

Studio apt. No shared walls. 7-min drive from the Village at Sunriver on S Century, 20 mins to Bend. Close to the Deschutes river. SUPs (2), kayaks (2), floats, rafts and bikes (2 adult and 2 kid), snowshoes (4 pairs). Pepper is a golden/boxer mix who loves kids and dogs. 25-mins to skiing at Mt. Bachelor. Private marina access in Oregon Water Wonderland. Pet friendly (no fee), fenced, hot tub, fire pit, horse shoes, putt putt, disc golf, movie theatre/golf sim (game room) upon req.

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, 200 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.

4.94 out of 5 average rating, 101 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 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.

4.92 out of 5 average rating, 105 reviews

Romantic Luxury w/Hot Tub, Amazing Lake Views

Stunning, romantic luxury cabin (2 bedr 2.5 bath, sleeps 5) on private Tumalo Lake w/cozy wood-burning stove, private hot tub, fire pit and 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, skiing, snowshoeing, hammock, horseshoe and corn hole game. Need more space? We also have 3, 4 and 6 - 8 bedroom cabins.

4.93 out of 5 average rating, 182 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 kayak rentals in Bend

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, 124 reviews

Large Black Bear Cabin in Three Rivers w/ wildlife

A spacious living area features comfortable seating arrangements on a patterned rug. Natural light fills the room through large windows, and a television is mounted above a cozy fireplace. Decorative elements include plants and artwork, contributing to a welcoming ambiance.

4.98 out of 5 average rating, 41 reviews

Quiet Family Home in the Trees

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

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.

5 out of 5 average rating, 50 reviews

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

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, 121 reviews

Wooded river retreat near Sun River & Bend

An open living area showcases a large wooden dining table with black chairs, accompanied by a cozy seating arrangement featuring a light-colored sofa and a dark sectional. Tall windows provide natural light and views of the surrounding trees, while a modern ceiling fan enhances air circulation.

4.9 out of 5 average rating, 194 reviews

Walk to SHARC 3BR Hot Tub

A cozy fire pit encircled by seated lounge chairs is visible in the foreground, with a tranquil outdoor space beyond. Trees and string lights enhance the setting, while a hammock and American flag are located in the background against a two-story cedar-sided home.

4.93 out of 5 average rating, 55 reviews

Mt. Bachelor & Sun River Get Away - 2025 Upgrades

A scenic view from the balcony showcases the Deschutes River alongside well-maintained buildings. The landscape is adorned with trees and soft grass areas under a clear blue sky, inviting relaxation and connection with nature.

5 out of 5 average rating, 29 reviews

A Stone's Throw | Crestline View

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.

4.94 out of 5 average rating, 51 reviews

Riverwoods A-Frame

A circular fire pit surrounded by six metal chairs is situated in a gravel area. A pathway leads from the fire pit to a two-story lodge, which features a balcony and large windows. Towering pines are visible in the background, and the sky displays hues of sunset.

4.75 out of 5 average rating, 20 reviews

Deschutes River Home | Game Room + Kayaks

4.95 out of 5 average rating, 39 reviews

A-frame w/ Cedar Hot Tub -avail now for ski season

5 out of 5 average rating, 3 reviews

AC Hot tub Luxury cabin pets allowed, perks, view!

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, 106 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

4.42 out of 5 average rating, 26 reviews

Private La Pine Cabin Rental: 30 Mi to Bend!

Other holiday 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.

Apartment 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.

Apartment in Bend

Otterspot on the Deschutes River w/Hot Tub

A spacious living area is highlighted by a stone fireplace surrounded by large windows that invite natural light. Comfortable seating includes leather couches and armchairs arranged around a glass coffee table. A warm, patterned rug adds a touch of coziness to the setting.

4.71 out of 5 average rating, 7 reviews

4 Bed/ 3 Bath, Pet Friendly, River Access , 5 Min

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.

4.9 out of 5 average rating, 94 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

4.83 out of 5 average rating, 12 reviews

SHARC 8 Hot Tub A/C Bikes Kayaks Tubes BBQ Village

4.92 out of 5 average rating, 52 reviews

An open living space features a large, dark blue sectional sofa and two matching armchairs. A wooden coffee table sits in the center, positioned over a soft area rug. Natural light filters through large windows, highlighting the wood-paneled walls and giving warmth to the inviting atmosphere.

Home in Sisters

Sisters Woodland Lodge- Hot Tub | Family Friendly

A spacious gourmet kitchen is highlighted by a central island with a gas stove. Natural wood cabinetry and a large window frame offer views of the surrounding trees. A dining table, surrounded by wooden chairs, invites gatherings, while a cozy area rug adds warmth to the space.