Vacation rentals with a kayak in Portland

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Top-rated kayak rentals in Portland

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Top guest favorite

A vibrant red couch is placed against a light-colored wall, accented by dynamic artwork mounted above it. A soft white throw blankets a nearby chair, complemented by a wooden side table and a lamp casting a warm glow. Natural light enters through a window, enhancing the lively decor.

Guest suite in Portland

4.97 out of 5 average rating, 491 reviews

Underground Art Suite

Spacious underground art suite/apartment in the sunlit basement of our 1926 bungalow in the lively SE Foster Powell Neighborhood. We partner with local artists to bring rotating artwork to the space. Enjoy a relaxing guest suite with a private entrance, parking and access to nearby food carts, restaurants, bars, galleries, and shops featuring local wares art & food. The space is a newly finished one bedroom modern guest suite with full kitchen, located in a quiet yet fun and funky neighborhood.

Top guest favorite

A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.

Guest suite in Milwaukie

4.95 out of 5 average rating, 427 reviews

River Forest Lake Apt w/hot tub. HOT find!

*No smoking, no parties, no drugs or pets on premises* total/Max 4 guests; included in this total are infants/children, no more than 2 or3 children under 12, as long as only 4 total guests. FYI: Incline driveway Welcome to our newly remodeled daylight basement apartment. Tucked into the quiet peaceful River Forest neighborhood of Milwaukie on River Forest Lake. Conveniently located to shopping, restaurants, hwy 99, freeways to Portland, Oregon City, historic Sellwood, the Gorge, Mt Hood, etc.

Guest favorite

Barn in Brush Prairie

4.96 out of 5 average rating, 157 reviews

Hockinson Carriage House - You Won't Want to Leave

Your stay can be as peaceful and relaxing as you desire. The property invites exploration at your leisure. The Carriage House is private and comfortable. You are a mile from the little town of Hockinson with a store, gas and a tap room. You are 6 miles from Battleground which offers all services and a neat downtown for shopping, antiquing, a winery and multiple restaurant options. Stay a night or stay and use as a base to explore Portland, Columbia River Gorge, Multnomah Falls, Vancouver.

Guest favorite

The living room features a spacious arrangement with a blue sofa and a bright yellow armchair. A patterned area rug anchors the space, while large windows allow natural light to illuminate the room. A small television and potted plants add to the welcoming atmosphere.

Cottage in Southwest Portland

4.91 out of 5 average rating, 125 reviews

The Victorian Cottage with River & Mountain Views

Welcome to The Victorian Cottage, a victorian influenced architecture, in a serene retreat in the picturesque West Hills of Portland. Prepare to be captivated by breathtaking vistas that encompass the majestic Mt. Hood, Mt. St. Helens, the meandering Willamette River, and the tapestry of Downtown Portland. For those who rise with the sun, witnessing its ascent over Mt. Hood from the balcony is an unforgettable spectacle that simply must not be miss. The Victorian Cottage is located on a hill.

Top guest favorite

A cozy seating area is highlighted by a warm brown sofa, complemented by a patterned armchair and a small side table. An open kitchen space is visible in the background, featuring a bar with three stools and natural light streaming through large windows.

Farm stay in Newberg

4.94 out of 5 average rating, 110 reviews

The Cellar @Lively Farm

Enjoy our little slice of hobby farm heaven nestled among the old-growth forest along Chehalem Creek. You'll experience the beauty of nature, the antics of our goats, chickens, rabbits, geese, ducks, and quail, and the charm of downtown Newberg. Our secluded neighborhood offers the perfect area for walking, running, or bike riding, and the wineries of Dundee are so close! Be warned that we live on the edge of the forest. Owls, deer, raccoons, squirrels, possums, and foxes frequent our yard.

Guest favorite

Three kayaks in vibrant hues of purple, red, and blue are arranged against a wooden fence, partially shaded by a tree. The surrounding area features reddish-brown mulch and dappled sunlight filtering through the leaves.

Guesthouse in Milwaukie

4.88 out of 5 average rating, 177 reviews

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

Superhost

The exterior of the home is highlighted by a multi-level design, featuring a spacious balcony overlooking a landscaped entrance. Surrounding trees provide privacy, while the steps lead to a welcoming front door. Colorful recycling bins are positioned at the bottom of the stairs.

Guest suite in Southwest Portland

4.87 out of 5 average rating, 175 reviews

Portland Hillside Retreat near OHSU & river

This comfortable home, nested in a forest setting and located in a great central, and safe neighborhood. The space is functional, and well appointed. You’ll have a super functional kitchenette, private bathroom, living room / work space / dining area, along with two, full bedrooms, and a very comfortable pull-out sofa that offers the space of a queen. Well stocked amenities with customization available on request. Within walking distance of the river, park, trails, and OHSU.

Top guest favorite

A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.

Guest suite in Milwaukie

4.95 out of 5 average rating, 177 reviews

Riverside Cottage Apartment.

Charming cottage apartment on a hill next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Guest favorite

A welcoming front porch area features comfortable seating set against natural greenery. A gravel path leads to a landscaped garden with a variety of plants, while outdoor lighting provides soft illumination. The large windows of the house overlook this tranquil setting.

Home in Aurora

4.89 out of 5 average rating, 163 reviews

Marvins Gardens & Pond in Antique and Wine Country

3 bedroom 2 bath house in Aurora, access to our pond, gazebo and dock that was the former Aurora Trout Farm. 25 miles to Salem and 25 miles to Portland only 2 miles off of I-5. Walking distance to the famous Aurora Antique shops and a small winery. 18 miles from Dundee Wine Country. One exit away from Factory Outlet Stores. Shuttle to and from Aurora Airport (KUAO) for a small fee. Come feel the peace of Marvin’s Garden’s and Trout Farm!

Top guest favorite

A dock extends over calm waters, featuring two lounge chairs positioned for relaxation. A kayak and two paddleboards are secured nearby, with a small storage area visible on the dock. Surrounding greenery reflects softly in the water's surface.

Guesthouse in Milwaukie

4.99 out of 5 average rating, 348 reviews

River Forest Guest House, All new+Riverfront Patio

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.

Top guest favorite

The lodge-style home is set against a backdrop of towering trees and lush greenery. A pathway leads to the front entrance, framed by ornamental plants and rocks. Natural light filters through the foliage, creating dappled shadows on the driveway.

Home in Oregon City

5 out of 5 average rating, 111 reviews

Highland Park- secluded lodge near the city.

Fabulous lodge style home on 5 park-like acres with a small lake, outdoor fireplace, game room and tv room. Just 30 min from Portland and the airport. Sleeps 10. Main level; master with king bed and bath, one bedroom with twin beds, (can be converted to king), one bedroom with queen bed, two baths. Upstairs, one bedroom with king bed and bath, one room with queen hideabed, shared bath.

Top guest favorite

Guesthouse in Tigard

4.95 out of 5 average rating, 210 reviews

The Cottage at River Run!

Welcome to the Cottage at River Run! Your private oasis nestled on 1.8 acres backing the Tualatin River. This cottage comfortably sleeps eight with an upper loft area with a full bed and two twin beds and views of the river! The lower level has a private deck, kitchen, 3/4 bath, queen Murphy bed and full sofa bed.