Holiday 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.

4.98 out of 5 average rating, 126 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, 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, 123 reviews

The exterior of a log cabin is showcased, featuring a spacious outdoor seating area with a fire pit. Comfortable lounge chairs and a dining space are positioned near a hot tub, with tall pines providing a natural backdrop. Warm lighting enhances the welcoming environment.

Cabin in Sunriver

On Deschutes River | Kayak | HotTub | EVCharger

Make some memories at @YourRiverfrontRetreat - a unique and family-friendly place . This cabin is located on the Deschutes river with a private dock and access - with provided kayaks, canoe, paddleboards and tubes. It is 30 minutes from Mount Bachelor and 8 min from the Sunriver resort, with tons of access to the outdoors. Enjoy your private hot tub and fire pit after a fun filled day. Enjoy the beautiful starry sky on a clear night. A perfect place to relax, spend time with family/friends, and/

4.93 out of 5 average rating, 282 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.

4.93 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

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, 183 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.

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, 205 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 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.

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.

4.84 out of 5 average rating, 121 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, 183 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.

4.98 out of 5 average rating, 167 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

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday 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 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

Superhost

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

4.9 out of 5 average rating, 194 reviews

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.

Home in Sunriver

Walk to SHARC 3BR Hot Tub

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.

4.97 out of 5 average rating, 60 reviews

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

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

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, 52 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.

4.76 out of 5 average rating, 21 reviews

Deschutes River Home | Game Room + Kayaks

4.95 out of 5 average rating, 40 reviews

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

Superhost

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

4.88 out of 5 average rating, 295 reviews

A serene sunset over the Deschutes River is captured, featuring vibrant colors reflecting on the water. Chairs are positioned along the sandy beach, framed by natural vegetation and trees, offering a tranquil riverside view.

Cabin in Old Bend

Amazing, unobstructed River View Downtown Bend

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

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, 54 reviews

Perfectly located getaway! Walk to the river!

4.97 out of 5 average rating, 95 reviews

A classic two-story home is presented against a vibrant sunset sky. The wrap-around porch features white columns and is surrounded by neatly trimmed shrubs. Large windows face the yard, allowing for ample natural light to enter the living space.

Home in Sisters

Downtown Pine Mountain Paradise

A spacious living area features a dark sectional sofa adorned with decorative pillows. A wooden coffee table is positioned in front. The kitchen and dining area are visible in the background, with wooden cabinetry and a dining table set for six. Natural light enters through large windows.

4.94 out of 5 average rating, 18 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.

4.9 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

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

Superhost

Home in Sunriver

4.83 out of 5 average rating, 12 reviews

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