
Holiday rentals with a kayak in Bend
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Bend

Total holiday rentals
Explore 30 holiday rentals in Bend

Nightly prices starting at
Bend holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 3,360 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Bend holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Bend rentals

4.9 Average rating
Bend stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Bend’s top spots include Old Mill District, Drake Park and Pilot Butte
Top-rated rentals with kayak in Bend
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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/

Riverfront Cabin w/ Private Dock & HotTub
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 H20 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.

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

River Run Bend Bungalow & Romantic Spa Grotto
Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

Paradise Found Near Sunriver & Big Deschutes River
Enjoy the entire spacious second floor in our beautiful custom home in the Sunriver area; includes 2 bedrooms, bath, bonus room with kitchen, loft.a huge landscaped fenced back yard with hot tub,fire pit,lots of seating that backs up to forest service land for you to enjoy.. Minutes from Sunriver Resort, one block from the Deschutes River, 30 min to Mt. Bachelor Enjoy the many rivers, lakes and hiking . We love sharing our home to quests . we live in the home but give our guests privacy.

Pepper’s Place
Private marina & hot tub — cozy, relaxing studio Apt with no shared walls, just outside Sunriver Resort on a fenced acre, 20 mins to Bend and 25 mins to Mt. Bachelor. SUPs (3), kayaks (2), floats, rafts, bikes (3 adult + 2 kid), and snowshoes (4 pairs). Pepper is a friendly golden/boxer mix who loves kids and dogs. Pet friendly (no fee), fenced yard, hot tub, propane and wood fire pits. Sound-deadened movie theater and foosball room available upon request. Backyard is shared with Pepper.

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.

Downtown Pine Mountain Paradise
Classic Pine Meadow Paradise! 3 bedrooms and an additional ADU, this consists of one King bed, two Queen beds and two twin beds. You will love all of the natural light and french doors right off the living room. Fully equipped kitchen with Island. Master bedroom has mountain views, sandstone shower and soaking tub upstairs. There is also a private ADU over the garage guests are free to use. Enjoy sitting around on the wrap around porch with your favorite drink with family and friends.

Location! Bungalow River & Beach Access
Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

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!

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.

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
House rentals with a kayak

Large Black Bear Cabin in Three Rivers w/ wildlife

Riverfront Cabin

Deschutes River Getaway-near Bachelor & Sunriver

Sunriver Luxury Family Home at Caldera Springs

Wooded river retreat near Sun River & Bend

Pet-Friendly Riverfront Home w/ Deck

Best for Old Mill:River Trail, Views & Town

Treehouse Retreat • Hot Tub • Near Sunriver
Cabin rentals with a kayak

Black Butte Ranch Ridge Cabin 022

Riverwoods A-Frame

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

Summer Waterfront Fun with Hot Tub & Water Toys

Tall Pines Guest House comes with rental canoe

Rustic cabin on the Big Deschutes River

Sunriver/Bachelor *RiverFront* Cabin

Risa Cabin: Full Lodge | Lake, Hot Tub, 9 Acres
Other holiday rentals with a kayak

Epic Waterfront Home, walk to Downtown & Old Mill!

Cascade Retreat - Designer Remodel Luxury

Riverfront Retreat w/ hot tub minutes to Sunriver

Cedar Retreat Waterfront, Spa 4Bed

Cozy Queen, Private Bathroom and Entryway

New! Brand New Furniture~Close to Trails~Fireplace

Peaceful Hobby Farm, Gateway to Outdoor Adventure

Mt. Bachelor & Sun River Get Away - 2025 Upgrades
When is the best time to visit Bend?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 SGD | $214 SGD | $205 SGD | $183 SGD | $219 SGD | $256 SGD | $300 SGD | $301 SGD | $224 SGD | $209 SGD | $180 SGD | $217 SGD |
| Avg. temp | 2°C | 3°C | 5°C | 8°C | 12°C | 16°C | 20°C | 19°C | 15°C | 9°C | 4°C | 0°C |
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