Holiday 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.

4.97 out of 5 average rating, 499 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, 432 reviews

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

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.

4.9 out of 5 average rating, 343 reviews

A serene lake scene is captured, surrounded by lush green trees and a clear blue sky. Two kayakers can be seen enjoying the calm waters, reflecting the vibrant natural landscape. The tranquil setting highlights the inviting atmosphere of the area.

Guest suite in Milwaukie

Upstairs Rustic 1940s styled Studio Apartment

Great for water loving people! Private unit. Self checkin. Outdoor patio & yard. Wifi. Pet/animal free, allergy safe. Smoke free. Linens washed with Defunkify perfume free soap. Fully stocked kitchenette. .75 Bathroom (sink, toilet, large shower) Stocked w/ toiletries. AC in summer. Complimentary snacks! 1940's vintage furniture. Quiet neighborhood. Semi-industrial parking, as we run a pressure washing biz. Your unit is around the back on the 2nd floor. 1/4 mi to bus route at top of hill.

4.96 out of 5 average rating, 158 reviews

The exterior of a red barn-style building is featured, with a prominent white star design above the entrance. Two garage doors and multiple windows allow natural light. A stone pathway leads to a small seating area with two chairs, while a BBQ grill is positioned nearby.

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.

4.87 out of 5 average rating, 101 reviews

A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.

Home in Lents

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

4.98 out of 5 average rating, 82 reviews

A bright living area is equipped with a comfortable leather sofa and an area rug laid over hardwood flooring. Large windows allow natural light to illuminate the space, which features a dining table and chairs, complemented by a stylish ceiling fan and modern kitchen visible in the background.

Apartment in Vancouver

Upscale Lakefront ADU w/ Access to Pickleball Ct.

Take it easy at this unique and tranquil getaway on Vancouver Lake with a beautiful outdoor deck to enjoy the view. Enjoy the sunsets and the wildlife on the lake. Kayak, sail, paddle board, or canoe out your door. We have a six person barrel sauna available: fee. You will have access to our private pier & pickleball court. The ADU is above the garage with a private entrance, about 4 miles to downtown restaurants, parks, the waterfront, etc. House is on 1.5 acres. We have chickens & gardens.

4.91 out of 5 average rating, 126 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.

4.96 out of 5 average rating, 180 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

River Garden Cottage.

Charming cottage apartment on a garden and forest 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.

4.94 out of 5 average rating, 116 reviews

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

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.

4.88 out of 5 average rating, 181 reviews

A serene river view is visible, framed by lush trees and greenery. The clear water reflects the sky, while a gentle wake from a boat creates ripples. A sandy beach area is located in the foreground, alongside a manicured lawn and a fire pit.

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.

4.87 out of 5 average rating, 181 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.

4.89 out of 5 average rating, 168 reviews

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

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!

Popular amenities for Portland kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

A modern living area features a light-colored couch adorned with green and beige cushions. A coffee table sits atop a textured rug, surrounded by round poufs. A desk with a chair is positioned nearby, complemented by a flat-screen TV mounted on the wall.

Home in Hillsdale

5 out of 5 average rating, 4 reviews

Modern Apt Nestled in Lush Hills

4.92 out of 5 average rating, 78 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

5 out of 5 average rating, 111 reviews

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

Highland Park- secluded lodge near the city.

4.85 out of 5 average rating, 33 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.

A wooden deck extends over the water, featuring two blue lounge chairs positioned for relaxation. Lush green foliage surrounds the tranquil river, creating a serene outdoor environment. Natural light enhances the peaceful setting, inviting guests to enjoy the view.

Home in Vancouver

4.94 out of 5 average rating, 101 reviews

Floating Home on Columbia River w/ Provided Kayaks

4.98 out of 5 average rating, 62 reviews

A spacious living area showcases a combination of modern and rustic elements, with a large window allowing natural light to illuminate the space. A cozy seating area includes a grey couch and an orange leather chair, and a wooden coffee table sits in front of a fireplace, against a backdrop of wood-paneled ceilings.

Home in Lake Oswego

Lake Oswego Riverfront House with Paddle Boards

The exterior of a charming Craftsman home is presented, framed by lush green trees and landscaped with neatly arranged shrubs and mulch. A welcoming porch is visible, with steps leading up to the entrance, highlighting the architectural details of the home.

Home in Westmoreland

4.72 out of 5 average rating, 50 reviews

Modern Boho Subunit in Stunning Sellwood-Moreland

5 out of 5 average rating, 6 reviews

A spacious entryway features hardwood flooring and a stairway with decorative railings. Natural light floods in through large windows, illuminating the area. A decorative fountain is positioned near the entrance, with wooden double doors leading to an outdoor space.

Home in Milwaukie

Splendor_Top Level|RIVR FRT|3BD

Other holiday rentals with a kayak

4.87 out of 5 average rating, 386 reviews

The guest room features a queen bed with crisp linens, a wooden frame, and a hanging canvas hammock nearby. A wooden table and upholstered chair are positioned beside the bed. Decorative wall art and colorful rugs highlight the space, with natural light filtering through the window.

Private room in Buckman

Mill Room @ 1234 HOUSE in SE PDX

A comfortable bedroom is presented, featuring a queen size bed with fresh bedding, two nightstands, and a cozy blanket draped across the foot of the bed. A lamp on the nightstand provides soft illumination, while light-colored curtains frame the window.

Private room in Wilsonville

4.81 out of 5 average rating, 27 reviews

Private bedroom in Wilsonville - in a house

The entrance of the glamping tent reveals a cozy sleeping area with a queen bed, framed by light-colored curtains. A woven rug covers the wooden floor, and lanterns add a warm touch. A small bench sits at the foot of the bed, enhancing the rustic charm.

Tent in Estacada

4.85 out of 5 average rating, 73 reviews

City escape retreat. Unplugged.

A modern house is set against a vibrant sunset, surrounded by tall trees. A gently curving driveway leads to the entrance, framed by landscaped gardens. Soft lighting highlights the exterior’s details, while a covered porch provides an inviting entryway.

Home in Forest Park

5 out of 5 average rating, 3 reviews

Natural Oasis in NW Portland

Private room in Ridgefield

New place to stay

Amazing Farm Stay - Sharing tranquility

A well-lit hallway connects the living area and kitchen. A white futon with orange pillows is positioned on a plush gray carpet. The doorway leads toward a dining area illuminated by soft lighting, with a glimpse of a modern kitchen visible in the background.

Apartment in Hillsboro

4.62 out of 5 average rating, 29 reviews

The Spot on East Main St.

The tranquil river reflects a picturesque landscape of trees and quaint homes on the opposite shore. The scene captures vibrant autumn colors, with calm waters mirroring the serene surroundings, creating a peaceful atmosphere.

Private room in Milwaukie

Riverfront Oasis