Holiday rentals with a kayak in Bend

4.98 out of 5 average rating, 164 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, 118 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, 380 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, 292 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.

4.92 out of 5 average rating, 153 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.

4.94 out of 5 average rating, 134 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, 150 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, 224 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, 129 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, 195 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, 127 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

4.97 out of 5 average rating, 100 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

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 ⁂

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, 124 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

4.96 out of 5 average rating, 107 reviews

A serene view of the river is framed by a decorative metal fence, complemented by lush greenery and colorful flowers along the bank. The water reflects sunlight and the surrounding natural landscape provides a tranquil setting.

Home in Old Bend

Riverfront Getaway

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, 190 reviews

Bend Family Retreat • Treehouse • HotTub •GameRoom

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, 64 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.

4.81 out of 5 average rating, 26 reviews

Deschutes Riverfront Home with A/C, Game Room, Hot

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.

4.92 out of 5 average rating, 106 reviews

Romantic Luxury w/Hot Tub, Amazing Lake Views

4.66 out of 5 average rating, 87 reviews

New place to stay

Lodge w/ Private Lake, hot tub, ideal for Families

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

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 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!

Other holiday 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

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.

Apartment in Bend

WorldMark Bend Seventh Mountain Resort - 1BD Sleep

4.78 out of 5 average rating, 146 reviews

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 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.

Apartment in Sisters

Country House Condo with a View

A two-story white house with a sloped roof is set against a clear blue sky. Green grass covers the lawn, and tall pine trees provide shade. A wooden deck with railing is visible, along with a path leading to the entrance.

Home in La Pine

4.76 out of 5 average rating, 93 reviews

Little House on the River near Bend and Sunriver

4.95 out of 5 average rating, 19 reviews

Deschutes River Front Home