Vacation rentals with a kayak in Sheboygan County

Find and book unique kayak rentals on Airbnb

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Popular amenities for Sheboygan County kayak rentals

House rentals with a kayak

Guest favorite
An aerial view captures the serene landscape along the lakefront, with sandy beaches and a grassy park area dotted with trees. Picnic structures and pathways are visible, creating opportunities for outdoor activities. The lake shimmers under the golden glow of the setting sun.
Home in Random Lake
4.91 out of 5 average rating, 45 reviews

Oma's Beach House

HaileyRating, 5 stars3 months ago
The place was perfect for spending the weekend hanging out with friends. The heat wasn’t turning on to begin with, but the hosts were very responsive and took multiple steps to fix it and make us comfortable.
Top guest favorite
Home in Elkhart Lake
4.98 out of 5 average rating, 82 reviews

Fernwood Lodge: Your Elkhart Lakefront Retreat

vIctoriaRating, 5 stars2 weeks ago
Beautiful home on a beautifully wooded street with lake view.
Guest favorite
Home in Sheboygan Falls
4.95 out of 5 average rating, 19 reviews

“On The Water” the Sheboygan River Overlook

SrinivasanRating, 5 stars2 days ago
Place is compact, yet got all the amenities. Nice backyard with access to river, grill and place for campfire. Interior looks clean and pristine. Calm and beautiful place to stay
Guest favorite
A spacious backyard overlooks Lake Michigan, with lush green grass and a firepit area surrounded by seating. The view reveals tranquil blue waters and a clear sky, creating a serene outdoor environment perfect for gatherings.
Home in Sheboygan
4.97 out of 5 average rating, 139 reviews

Lake Michigan home with gorgeous views!

CraigRating, 5 stars1 week ago
We have stayed with Todd numerous times and I have to say each stay is a great experience. Thanks for being a great host..
Top guest favorite
A spacious house is nestled among vibrant trees in autumn colors. Large windows reflect the natural surroundings, while a covered patio with seating is visible in the foreground. Lush green grass envelops the property, enhancing the serene outdoor ambiance.
Private room in Cascade
5 out of 5 average rating, 43 reviews

Suite Retreat - Hideaway in the Woods ❤

RichardRating, 5 stars6 months ago
We were going to a wedding nearby, so we didn't get as much time as we would have liked to enjoy the deck/patio outside. The property is very property is very quiet and full of nature.
The exterior of a two-story house is displayed, showcasing a combination of gray siding and a brown roof. A landscaped yard features pink rose bushes and decorative rocks, complemented by tall grasses, creating a welcoming atmosphere.
Home in Sheboygan Falls
4.92 out of 5 average rating, 13 reviews

River Meadow Getaway in Sheboygan Falls

JohnRating, 5 stars32 months ago
Great location with quick access to all attractions in the area. Loved the calm setting of the yard and views from the house, so easy to unwind!
Guest favorite
A wooden dock extends into a tranquil pond, surrounded by lush greenery and flowering plants. The water reflects the blue sky and scattered clouds, while trees in full bloom line the bank, creating a peaceful natural setting.
Private room in Plymouth
4.85 out of 5 average rating, 179 reviews

A Bit of the "Lake" right in Town

ConstanceRating, 5 stars6 months ago
Thank you for everything, we spent a great weekend in your home. It was a great spot to enjoy fall and to hike around. The home is lovely with everything you would need while traveling ! And the price is really honest compared to everything else. I recommend it !
Top guest favorite
A serene view of Little Elkhart Lake is presented, featuring calm waters reflecting the lush greenery. A wooden dock extends into the water, accompanied by two wooden chairs positioned for relaxation. In the distance, a paddle boat and another dock are visible, enhancing the tranquil setting.
Home in Plymouth
5 out of 5 average rating, 63 reviews

Paddock Point Lakehouse. Road America+Hot Tub

JessicaRating, 5 stars6 months ago
This place was absolutely gorgeous and so well taken care of! The host Hillary was very responsive when I had questions and gave us some great recommendations for things to do in the area! We didn't get to spend much time at the house because we were there for an event but everyone agreed they would all love to come back when we don't have any plans to relax and enjoy the place! Beautiful house and beautiful view highly highly recommend!

Cottage rentals with a kayak

A serene lakeside view features a private dock extending into Crystal Lake, surrounded by lush greenery. Several boats are moored nearby, with calm waters reflecting the clear blue sky. The gentle shoreline is lined with grass, adding to the tranquil atmosphere.
Cottage in Plymouth
4.75 out of 5 average rating, 4 reviews

Crystal Lake Cottage: Kayaks & Fire Pit!

KellyeRating, 5 stars23 months ago
Lovely lake house, beautiful sunsets in the lake very peaceful. Just a few minutes to Road America Race way which was perfect for us! Thank you for letting us stay hope to see you again soon!
Guest favorite
A spacious deck features a hot tub and seating area with two armchairs and a coffee table. Lush greenery surrounds the space, offering serene views of Crystal Lake. Soft lighting strung overhead enhances the welcoming atmosphere.
Cottage in Plymouth
4.94 out of 5 average rating, 32 reviews

Lakefront Plymouth Cottage w/ Private Hot Tub

SeanRating, 5 stars1 month ago
Works can’t describe how beautiful and cozy being that close to lake were. It began snowing while we were in the hot tube. The lake disappeared little by little including the little island in the middle. Until it was virtually a white out! I can honestly check one off the bucket list it was amazing!
Guest favorite
A private pier extends into the calm waters, lined with colorful kayaks and paddleboards. The spacious lawn offers picnic tables and a view of the lakehouse's modern exterior, framed by lush greenery and tall trees under a clear blue sky.
Cottage in Random Lake
5 out of 5 average rating, 8 reviews

Cozy Lakefront Escape: Ideal Seasonal Getaway

CheyanneRating, 5 stars3 months ago
Such a beautiful and peaceful place. Host is very friendly and responsive. First time I’ve woken up feeling well rested in a minute, beds really helped any of our back issues. Main parking spots might not be available at first due to people parking there for ice fishing on the lake but plenty of street parking. If staying in the winter, run the water for a moment to run through any sediment in the pipes. (Not a house problem, just winter in Wisconsin.) :)
Superhost
The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.
Cottage in Random Lake
4.84 out of 5 average rating, 67 reviews

Private 3 bedroom lake house

HoaRating, 5 stars2 weeks ago
Awesome place. We will be back!

Cabin rentals with a kayak

Top guest favorite
The serene lakefront cabin is depicted, showcasing a wooden exterior that reflects in the calm water. Lush greenery surrounds the home, and the clear blue sky adds to the peaceful atmosphere. Balconies and windows enhance the cabin's inviting structure.
Cabin in Cascade
4.95 out of 5 average rating, 19 reviews

This is the place! Lakefront cabin for big family

CaitlinRating, 5 stars1 month ago
Our groups have been staying at Jennie's place for the last several years and always look forward to returning. The house is great for groups - lots of living and sleeping space for everyone. The set up is super fun with different floors and spaces to enjoy. The backyard is great for having a bbq or a campfire right on the lake. The area is nice and quiet as well as beautiful. Our groups are always impressed as soon as we pull up! The hosts are always available to answer quesitons and offer information and they always respond to emails/text super fast. We will definitely keep booking here!
Guest favorite
Cabin in Random Lake
4.95 out of 5 average rating, 91 reviews

The Random Cabin (On Random Lake)

SamRating, 5 stars1 month ago
Had a very relaxing couple of nights at Dan's place on Random Lake. It was a bit cold for us to go on the water but we enjoyed costing up to the lakeview by the fireplace.
A serene lake view is presented, featuring a wooden dock extending over calm waters. Lily pads are visible near the shore, while two boats are docked nearby, partially covered. Lush greenery lines the far side of the lake, enhancing the tranquil setting.
Cabin in Cascade
4.75 out of 5 average rating, 4 reviews

Sunset Views by Long Lake

DeniseRating, 5 stars6 months ago
The first words out of our 19 year old’s mouth was, “Mom, this is the best one we have ever stayed in!” Everyone loved how cozy the place felt and how you could set the temp for each room, just the way you liked it, including in the bathroom if the morning was a bit chilly. The rustic charm is just beyond beautiful. I loved the swing set and sitting area around back. Our dog loved it. Overall, just an absolutely gorgeous place to be for an entire week. The beds were clean and comfortable. I would highly recommend to anyone looking for a nice get away.

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