Vacation rentals with a kayak in Black Butte Ranch

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, 283 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, 144 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, 122 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

4.92 out of 5 average rating, 124 reviews

The modern A-frame cabin is set amidst tall pine trees, displaying a striking black exterior. Tall, triangular windows allow natural light to brighten the interior. A spacious deck wraps around the cabin, offering an ideal spot for outdoor relaxation.

Cabin in Sisters

Popular BBR A-Frame | 2 golf courses | 5 pools

Welcome to Your Modern A-Frame Cabin at Black Butte Ranch! - Accommodations: Sleeps 8 in 2 queen bedrooms and a 2 twin loft, and trundle downstairs - Amenities: Relax in the living area with a Roku TV; the chef's kitchen makes meal prep easy, and self check-in ensures a smooth arrival - Sunny Recreation: Access to 6 pools, including the nearby Paulina pool, plus golf, pickleball, horseback riding, and hiking - Winter Fun: 20m drive to HooDoo Ski Resort Book your unforgettable getaway today!

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.

4.92 out of 5 average rating, 140 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.

4.92 out of 5 average rating, 600 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.

4.92 out of 5 average rating, 210 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, 106 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.

4.85 out of 5 average rating, 123 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.

Popular amenities for Black Butte Ranch 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, 124 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

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

4.94 out of 5 average rating, 185 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

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

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

Superhost

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, 106 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

Cabin rentals with a kayak

4.9 out of 5 average rating, 485 reviews

A wooden deck provides seating with two Adirondack chairs facing the tranquil river. Potted flowers add a touch of color to the space, while lush greenery lines the riverbank. Kayakers can be seen leisurely paddling on the water under a bright blue sky.

Cabin in Old Bend

Mill Cabin at Deschutes Dunes River/ beach access

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, 55 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.

4.87 out of 5 average rating, 15 reviews

Riverfront Cabin w/ Trails, AC & Views

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

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

Other vacation 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, 21 reviews

Black Chair Inn

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

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!

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, 143 reviews

Country House Condo with a View

Superhost

An open living space features a blend of seating options, including a spacious orange sofa and wooden dining chairs. A large window allows natural light to brighten the room, while shelves and plants add a touch of decor. A cozy atmosphere is created by the arrangement of furniture.

4.78 out of 5 average rating, 9 reviews

The Red House

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.