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Vacation rentals with a kayak in Pennington County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Pennington County

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The exterior of the Sturgis Loft is shown, featuring a two-story structure above a two-stall garage. A spacious driveway extends in front, providing ample parking space. A covered balcony with seating is visible on the upper level, surrounded by a grassy area and tree line.

Home in Sturgis

4.89 out of 5 average rating, 128 reviews

Downtown Legendary Sturgis Loft

Rise 'N Shine brings you a newly updated loft home with 3 bedrooms (3 queen), 2.5BA, huge garage with bar, loads of parking, & 3 sliding glass doors that lead to the 40 foot balcony overlooking Main St Sturgis! This is a super fun and convenient spot that makes for an amazing vacation experience whether you're a family with kids, friend groups, or couples! Proximity to attractions & surrounding towns is impeccable with Mt Rushmore 45min, Deadwood 15min, Spearfish Canyon 15min, & Custer 1hr 15min

A single-story green house sits nestled among greenery, featuring a welcoming front porch with three light-colored chairs and a small table. Two windows allow natural light, and a stone wall leads to a gently sloped yard.

Cottage in Rapid City

4.95 out of 5 average rating, 20 reviews

Remodeled Home In The Woods, Just Past City Limits

Come enjoy the peace and quiet of this remodeled home in a canyon neighborhood setting conveniently located minutes from various trailheads, multiple lakes, and endless scenic roadways. Or just enjoy a peaceful walk or bike ride from your front door down the scenic Cleghorn Canyon. This location is also just a couple of miles from Rapid City's downtown including parks, restaurants, breweries, and shopping. This home is fully furnished with everything you should need including A/C and free Wi-Fi.

A living area showcases a cozy arrangement with a television on a stand, surrounded by comfortable seating including an armchair and a sofa. A wooden dining table is set with a neutral table runner, complementing the warm tones from the natural light filtering through the windows.

Home in Hill City

4.76 out of 5 average rating, 50 reviews

Dads 2 Bdr 1 Bath home Hill City 1 car garage

You'll feel at home in the hills nestled in this beautiful fully furnished 2 bdr 1 bath home. Renovated in 2019. Detached garage 1 bay . Sit on the wrap around porch and take in all nature has to offer including a stream, deer and turkeys. Close to all attractions in the Black Hills and Rapid City. Walk to downtown with its restaurants, quaint shops and art galleries. Micolson walking trail is right behind us. Parking galore. Owners occasionally may stay in the studio behind the detached garage

A well-designed kitchen features warm wooden cabinetry and granite countertops. Stainless steel appliances include a gas stove and dishwasher, while pendant lights provide illumination. A woven rug adds texture, and ample natural light flows in through windows, showcasing the scenic views beyond.

Cabin in Sturgis

4.9 out of 5 average rating, 111 reviews

Cliffside Lodge in Boulder Canyon-Spa-Golf-Private

Vanish into seclusion and serenity in this stunning mountain getaway in Boulder Canyon just outside of Sturgis. Stunning views, a fully stocked kitchen, beds you will melt into, and views of the Boulder Canyon Golf Course directly across from you. This magazine worthy gem offers guests the perfect homebase to explore the Black Hills from a central location and come home to retreat and recharge in a quiet and secluded setting surrounded by soaring pine trees and the stunning beauty of the forest

A modern tiny home features large windows and a deck overlooking a wooded area. Flower pots and rocks surround the entrance, while steps lead up to an outdoor seating area. The tranquil setting is enhanced by the lush greenery of the surrounding pine trees.

Tiny home in Rapid City

4.94 out of 5 average rating, 18 reviews

In the Pines

Welcome to your Black Hills getaway Brand New tiny home. You will be swept away by the swaying of the pine trees, beautiful scenery and abundant wildlife from your very own deck. Enjoy the starry night skies and PEACEFULNESS of being away from the city. Its time to relax, rejuvenate and cozy up in front of the fireplace in the bedroom loft. You are minutes from your next adventure whether it be hiking, biking, kayaking or sight seeing there is something for everyone. License#COVHRLIC25-0007

The spacious bedroom features a large bed with soft bedding, complemented by two bedside lamps. A wooden nightstand and a flat screen television are present. Storage is provided by built-in closets and a door leading to an adjacent area.

Home in Whitewood

5 out of 5 average rating, 53 reviews

Sassy Pines Centralized Black Hills Home

Enjoy this spacious home in the epicenter of the Hills. The perfect homebase to visit attractions & a guest favorite for families w/ kids and pets. Super private & renovated beautifully, large yard w/ mature shade trees, & a 1 min walk to the local hot spot Bullwhacker's Restaurant & Bar. Wooded park, hiking & walking trails, picnic areas & a sledding hill in town! This one has a LOT to offer families & there's more to come! Located 15min to Deadwood, 7min to Sturgis, 25min to Rapid City

A firepit is surrounded by several adirondack chairs, where people are engaged in roasting marshmallows. The grassy area is framed by trees and a distant structure, enhancing the outdoor ambiance. The firepit's flames provide warmth and an inviting glow to the gathering.

5 out of 5 average rating, 11 reviews

French Creek Hideaway. Game room, creek, 10 acres

A wonderful escape. 6 miles to Custer city. 3 miles form Custer State Park Entrance and Stockade lake. 2 mini split AC units for your comfort. French creek flowing on the property for your enjoyment. 4 bedroom house (7 beds total). Includes 18 foot tipi, foos ball table, poker table, arcade, ping pong and 10 acres. Backed up to forest service for endless hiking and exploring. Outdoor decks with seating and a firepit, barbecue and gas grill. Relax and enjoy the beautiful Black Hills

An aerial view of a cabin that features a wooden exterior with green accents. A spacious deck is visible, furnished with chairs, and flags of Norway and the United States are displayed. The surrounding area is framed by tall pine trees, creating a natural setting.

Cabin in Rapid City

5 out of 5 average rating, 5 reviews

Black Hills Cabin Great Central Location-WIFI

The Black Hills are often underestimated because of the word "Hills". The facts become apparent as you wind your way up hairpin turns high up on Edelweiss Mountain. The 1500 sq. ft. three-bedroom cabin is located at (5600 ft elevation) above sea level in the heart of the Black Hills National Forest. The cabin is located among the pine trees on Edelweiss Mountain just twelve miles north of Hill City South Dakota and three switchback country miles off of the scenic U.S. Highway 385.

Top guest favorite

The modern kitchen features wooden cabinetry and stainless steel appliances. A spacious island with two high-backed stools provides seating. Decorative signs adorn the walls, complementing the inviting design. The floor showcases polished wood, while a runner rug adds a touch of comfort.

Home in Sturgis

5 out of 5 average rating, 7 reviews

SturgisRusticHome5bed

1 mile from downtown Sturgis, this spacious 5-bedroom home blends rustic charm with modern comfort—perfect for groups, riders, or families. With 9 beds including a sofa sleeper upstairs, it sleeps up to 16. Enjoy a full kitchen open to dining and living areas, 3 full baths, master with a king bed. Other rooms have a king, 2 queens, 4 twin beds. Includes garage for 12 motorcycles, patio, yard, BBQ grill, and fire pit. A perfect home base for the Black Hills or the Sturgis Rally.

The rustic cabin is situated among natural greenery, surrounded by towering trees and rock formations. A spacious front porch leads to the entrance, framed by steps. A deck extends from the side, providing outdoor seating options amidst the serene forest setting.

Place to stay in Hill City

4.89 out of 5 average rating, 27 reviews

DRY Historic China Gulch Cabin

Ready to unplug? Located right off the highway, this rustic DRY cabin offers a true back-to-basics escape—with ties to Mt. Rushmore’s first roads and the Black Hills’ first woman doctor. No running water, AC or plumbing, just power, a fire stove, and an outhouse. Perfect for hikers and nature lovers. Start your day with a cup of Joe on the porch, then hit nearby trails. End it under the stars on the back deck or cozied up by the fireplace. Simple, rugged, and close to nature.

A rustic grain bin structure is highlighted, showcasing its metallic exterior and round shape. A vibrant blue door features welcoming text. Two outdoor chairs with cushions sit on a gravel pathway, inviting guests to relax while enjoying the surrounding landscape.

4.88 out of 5 average rating, 32 reviews

Bin2Quinn

Enjoy a unique South Dakota experience! Stay in a custom designed, fully furnished grain bins! Featuring a spiral staircase to a Queen size bed. connected bin has another bedroom with one Queen Bed and Twin bunk beds. Bathroom with a shower. Coffee bar, tv and other amenities inside of the grain bin. We also have an outdoor seating grain bin with a fire pit and a gorgeous view! Plus, enjoy a private lake with an outdoor seating area and free kayaks for your use.

Top guest favorite

A white tray is placed on a textured beige blanket, featuring the word 'WELCOME' prominently. A blue glass vase holds lavender stems, and a colorful notebook rests beside it. The background highlights soft blue pillows and patterned throw cushions on a spacious bed.

Home in Rapid City

5 out of 5 average rating, 18 reviews

The Rushmore Home close to DT Rapid/near Sturgis

Stay comfortable at this peaceful and centrally-located abode that is nestled in the beautiful Black Hills of SD. One min to hospital, 5 min from downtown, 30 min from Sturgis, and 30 min from Mount Rushmore. We have two fantastic dogs that we share our home with. Very large fenced-in backyard with city views. We are open to long term stays so travel nurses are welcome. Capture the essence of the Black Hills with us!

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Pennington County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

The exterior of a uniquely shaped stone house is highlighted, featuring a combination of natural stone and modern elements. Surrounding areas display various outdoor features, including a barbecue grill and multiple bathtubs, with landscaped stone and greenery providing a foundation for the structure.

Private room in Custer

5 out of 5 average rating, 6 reviews

The Loft. 7 guests, 1 room. Beautiful & peaceful.

Top guest favorite

The exterior of a newly constructed house features a symmetrical façade with a light gray garage door and a neatly landscaped front yard. The driveway is paved, and small shrubs are arranged along the pathway leading to the entrance, framed by grassy areas.

Private room in Rapid City

4.97 out of 5 average rating, 87 reviews

Quiet~Cozy~Spacious Lower-Level, 5 min from I-90!

An entryway features rich wooden door frames and polished hardwood floors. To the right, a decorative wall piece adds character, while a flower arrangement in a planter resides on the floor near the entrance mat. The overall setting suggests a blend of historical charm and welcoming design.

Home in Whitewood

4.93 out of 5 average rating, 69 reviews

The Rustic Rose Condo

A modern living area features a combination of a light-colored sofa and two red accent chairs. A wooden wall adds warmth, while large sliding glass doors open to the outdoor view. A small coffee table and a warm lighting fixture complete the inviting space.

Home in Rapid City

Mid-Century w/ views & privacy

The exterior view of a cozy bungalow is presented, featuring a red-painted deck and staircase leading to the front entrance. Lush greenery surrounds the home, while a small storage shed is visible to the side. The architecture reflects a blend of historic charm and modest updates.

Home in Deadwood

4.75 out of 5 average rating, 32 reviews

Deadwood Main Street Retreat: Fun & Convenient!

Top guest favorite

A spacious backyard is enclosed by privacy fences, featuring a well-manicured lawn. A deck is visible alongside a picnic table, while chairs and a swing set offer additional seating options. The yellow exterior of the house adds a touch of warmth to the outdoor setting.

5 out of 5 average rating, 17 reviews

Dwntwn Custer Farmhouse on Main St. with Hot Tub

The exterior of the vacation rental features a welcoming entrance with steps leading up to a large glass door. A railing surrounds the steps, and manicured lawns enhance the curb appeal. Trees provide shade, while a nearby building complements the home's design.

Home in Hill City

5 out of 5 average rating, 11 reviews

Hill City Haven Downtown Main Street

The exterior of the home features a large porch with wide steps leading up to the front entrance. A verdant lawn is bordered by trees and shrubs, providing a natural setting. The structure is two stories, with multiple windows allowing for ample light.

Summit Hideaway- Forested, Amazing Views, Private

Other vacation rentals with a kayak

A rustic grain bin structure is highlighted, showcasing its metallic exterior and round shape. A vibrant blue door features welcoming text. Two outdoor chairs with cushions sit on a gravel pathway, inviting guests to relax while enjoying the surrounding landscape.

4.88 out of 5 average rating, 32 reviews

Bin2Quinn

The exterior of the Sturgis Loft is shown, featuring a two-story structure above a two-stall garage. A spacious driveway extends in front, providing ample parking space. A covered balcony with seating is visible on the upper level, surrounded by a grassy area and tree line.

Home in Sturgis

4.89 out of 5 average rating, 128 reviews

Downtown Legendary Sturgis Loft

A vintage framed album cover features a prominent image of a man in a suit, alongside bold colors of red and yellow. The title 'Greatest! Johnny Cash' is displayed prominently, evoking a classic music era. The composition is enhanced by a decorative border, enriching the nostalgic theme.

Apartment in Custer

4.91 out of 5 average rating, 33 reviews

NEW Johnny Cash on Main Walk to Downtown

The living room is characterized by multiple leather sofas and a mounted flat-screen TV. Floor-to-ceiling windows provide natural light, complemented by a fireplace and rustic decor. A solid wood dining table is visible, enhancing the spacious open layout.

Vacation home in Whitewood

4.97 out of 5 average rating, 78 reviews

The Whispering Buffalo Condo

The front entrance features a striking red door framed by a portico, complemented by white columns. Two planters sit on either side of the steps, and landscaped greenery surrounds the entrance, with a brick pathway leading to the door.

Home in Rapid City

4.75 out of 5 average rating, 71 reviews

Red Door BNB

The exterior of the vacation rental features a welcoming entrance with steps leading up to a large glass door. A railing surrounds the steps, and manicured lawns enhance the curb appeal. Trees provide shade, while a nearby building complements the home's design.

Home in Hill City

5 out of 5 average rating, 11 reviews

Hill City Haven Downtown Main Street

A vintage bicycle with a front basket rests against a large windmill structure under a shaded tree. The surrounding area features lush green grass and a tree line in the background, with a building partially visible along the driveway.

Guesthouse in Hermosa

4.91 out of 5 average rating, 96 reviews

Rushmore Retreat, Enjoy Quiet! Place to Yourself!

The spacious kitchen features hardwood flooring and stone accents. A large island with four bar stools provides ample seating. Modern appliances are integrated among rich wooden cabinetry, while light fixtures illuminate the area. Glass doors open to a sunroom with forest views.

Cabin in Sturgis

4.92 out of 5 average rating, 50 reviews

Deadwood Mountain Top Hideaway

Destinations to explore