Vacation rentals with a kayak in Portland

Guest suite in Foster-Powell

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.

4.96 out of 5 average rating, 464 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.

4.95 out of 5 average rating, 414 reviews

Guest suite in Milwaukie

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.

4.98 out of 5 average rating, 205 reviews

A serene view of a pond framed by lush trees, revealing two kayaks and a small rowboat docked along the grassy shoreline. The clear water reflects the surrounding greenery under bright sunlight, inviting a peaceful outdoor experience.

Treehouse in Mt Hood

Beautiful, Magical, Treehouse

"Glamping at its' best"! 16' x 16' TreeHouse, suspended between 3 large fir trees, queen size bed, loft w/2 twin beds, composting toilet, much more, situated on 20 acres with a pond. Gas heater, mini-fridge, microwave, coffee pot. IMPORTANT: this is a Tree House! Going up the spiral staircase is an adventure in itself, so pack small bags (or packs) (large suitcases are not appropriate). Be sure to look at the pictures & read our reviews... that provides the most information. Happy Travels!

4.94 out of 5 average rating, 110 reviews

The exterior of a modern home is showcased, featuring a wooden pergola adorned with string lights that create a warm ambiance. A patio area includes seating and a grill, surrounded by lush greenery and forested terrain.

Home in Washougal

Forest+River Haven @ Timber Moon Cabin w/ Hot Tub

Timber Moon is a modern Washougal River Getaway. Nestled in over 10 acres of Washington State Forest with secluded access to the Washougal River out your back door. You'll instantly feel the rhythm of nature when you arrive. Just a beautiful one hour drive from Portland. ✴ Hot Tub at the edge of the forest ✴ Dougan Falls 10 min walk ✴ Naked Falls 5 min drive ✴ Yacolt Burn State Forest 1 mile away ✴ Columbia River Gorge 15 min drive ✴ Starlink high Speed WiFi ✴ Pet Friendly *Please note

4.96 out of 5 average rating, 152 reviews

Barn in Brush Prairie

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.

4.92 out of 5 average rating, 118 reviews

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 Portland

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.

4.87 out of 5 average rating, 174 reviews

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

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.

4.88 out of 5 average rating, 163 reviews

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 Portland

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.

4.95 out of 5 average rating, 171 reviews

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

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.

4.99 out of 5 average rating, 341 reviews

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

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.

5 out of 5 average rating, 107 reviews

A serene lakeside scene is captured, featuring a rowboat and a yellow kayak neatly resting against the shoreline. Lush green trees are reflected in the still water, enhancing the natural beauty of the surroundings.

Home in Oregon City

The Secluded Lodge at Highland Park

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.

4.95 out of 5 average rating, 205 reviews

Guesthouse in Tigard

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.

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Popular amenities for Portland kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 29 reviews

Large clusters of white flowers bloom on green foliage, creating a vibrant contrast against a rustic barn with a corrugated metal roof. The barn's weathered structure and a small cupola are visible in the background under a clear blue sky.

Home in Vernonia

Farmhouse rest and relaxation

NicoleRating, 5 stars3 weeks ago

Jeff and Susan's farmhouse is an absolute gem in the Airbnb world! We stayed here for 4 nights during our family reunion. Although we filled the house with 9 adults and a baby, there was still plenty of space to relax, play games, and enjoy family meals both indoors and outdoors. Everything about the farmhouse is welcoming. It is well-stocked with everything you can possibly need, and they even left homemade cookie dough for us in the refrigerator! The fantastic outdoor patio area not only has a firepit and grill, but also its own fridge and sink. The gardens were stunning, and we enjoyed the birds and rm animals. Susan and Jeff are delightful and friendly, but very courteous of the privacy of their guests. We participated in a yummy jam tasting session w/ Susan, and went home with a few jars from her business next door. We also really appreciated how clean and tidy the home is kept. This is the best place to stay if you are visiting Vernonia. If not, this is a destination in itself!

5 out of 5 average rating, 3 reviews

A modern farmhouse is nestled among tall trees, featuring large windows that illuminate the exterior with a warm glow. The structure showcases a natural wood facade and a charming roof, while outdoor lighting adds to the inviting ambiance of the retreat.

Home in Estacada

Mt. Hood Retreat on Private Mountain Lake

RezaRating, 5 stars2 weeks ago

This was my second time staying on Jeremy’s magical property, and this time we brought the whole family! We rented both the main house and guest house for a weekend getaway, and the experience was absolutely unforgettable. The main house is warm, inviting, and incredibly spacious—perfect for gathering everyone under one roof. The design is thoughtful and full of charm, with cozy corners, a well-stocked kitchen, and comfortable beds throughout. We cooked, laughed, and shared meals around the dining table, then relaxed by the fire or explored the beautiful surroundings. The private lake, forest trails, wildflowers, and peaceful energy of this place make it feel like your own private nature retreat. We saw all kinds of critters, made bonfires, and enjoyed being completely unplugged. It was everything we hoped for and more. Jeremy’s hospitality is unmatched, and this property continues to be a favorite. We can’t wait to return again.

4.94 out of 5 average rating, 67 reviews

A charming two-story home features a welcoming front staircase leading to the entrance. The house showcases a white exterior with contrasting dark trim. Lush greenery and a well-maintained pathway enhance the inviting appearance, while large windows allow natural light to fill the interior.

Home in Camas

Camas Lakehouse With Private Hot Tub

NicoleRating, 5 stars2 weeks ago

We loved our family’s stay. The owners accommodated us and made us feel comfortable and welcome. The home is beautifully and comfortably furnished and designed.

CandiRating, 5 stars2 weeks ago

Home in Wilsonville

New place to stay

Cozy Vintage Farmhouse

What a beautiful property! The house is gorgeous and the large yard was perfect for the kiddos to play in. The space is thoughtfully decorated! My 5yr old daughter absolutely loved the little play area in the upstairs bedroom and our teenager loved the downstairs bedroom away from everyone else. The kitchen is dreamy! We had an incredible weekend and cannot imagine it better spent anywhere else! Thank you for sharing your home with us!

4.94 out of 5 average rating, 116 reviews

The front exterior of a one-level home is displayed, featuring a well-manicured lawn and a tree beside a concrete walkway. The house showcases light gray siding with white accents, a dark front door, and a two-car garage with a textured door. Clear blue skies frame the scene.

Home in Battle Ground

Chic home-explore outdoors PNW/Hike/Fish/wineries

SarahRating, 5 stars1 week ago

The house was absolutely perfect. The furnishings and decorations were just enough to feel homey without feeling like a specific person's home and therefore feel like an intrusion. There were snacks and many home amenities available, even ones you might not think of like plastic wrap, foil, and ziplock bags. The hostess checked on us via text when we had not checked in right away, and was understanding of why we didn't send a message right away. Any time we had questions or concerns she was quick to respond and was always polite and sincere. The location is situated in a quiet neighborhood. It is close to four different grocery stores and a number of fast food establishments. I have every intention of staying at this location again in the future if it is available at the desired time. It was a great experience all around.

4.83 out of 5 average rating, 24 reviews

The blue historic house features two stories with a wraparound porch. Bushes are neatly trimmed along the pathway, leading to the entrance. A grassy lawn adds to the outdoor space, complemented by the surrounding trees providing shade.

Home in Dayton

Ole Tyme B&B Warm setting with a country feel.

ElizabethRating, 5 stars7 months ago

Thank you Heath, you were a gracious host and it helped us in transition to our new house. Princess was the sweetest goat.

4.91 out of 5 average rating, 70 reviews

A hot tub is positioned on a deck, offering a view of a vibrant sunset beyond a modern home. Trees frame the scene, with soft lighting adorning the structure. The silhouette of a spiral staircase adds depth to the setting.

Home in Lents

RoofTop FirePit, HotTub & Outdoor Theater

KristenRating, 5 stars1 week ago

The most magical, relaxing and beautiful Airbnb I have ever stayed in absolute perfection view from the tower, and the fire pit is incredible. The hot tub is beautiful. There’s this incredible Koi pond with hammock chairs. most relaxed. I’ve been in months. The hostesses are just absolutely delightful friendly people. Could recommend this spot more. Can’t wait to have an excuse to come up and stay again.