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Family-friendly vacation rentals in West Pennington

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in West Pennington

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy bedroom features a spacious bed covered with a red blanket. Two framed artworks adorn the wall above the bed. A mounted TV is positioned nearby, while a light wood closet with double doors is visible to the right. Natural light enters through a window.

Guest suite in Rapid City

4.98 out of 5 average rating, 478 reviews

Quiet private suite with garage bay & kitchenette

Quiet private bedroom and kitchenette isolated from the main house with common use sun room between. Rural setting off Hwy 44 just minutes from Rapid City Airport. Tesla 11kw destination charging outlet in your garage bay directly accessible from the suite. Starlink 150mbps internet. Pet friendly to friendly pets with pet door from the suite out to the fenced back yard & patio isolated from our dog & cat. Private bath has in-floor heat and endless hot water with continuous flow water heater.

Top guest favorite

A charming red house is surrounded by lush green grass and tall trees, with a sloped hill rising in the background. A small deck with white chairs is visible at the front, offering a welcoming outdoor space.

Cabin in Hill City

4.94 out of 5 average rating, 113 reviews

Grandma's House in the Heart of the Black Hills

Grandma's House is in the heart of the Black Hills, located 1 mile from Hill City, it is minutes away from Mt. Rushmore, Crazy Horse, Custer State Park and more. It sits alone on the edge of a meadow with hills directly behind it and a small, bubbly creek in front of the house. It has plenty of room for kids to run and play outside, and a cozy, quaint inside for families to enjoy each other's company. Grandma’s House is available for extended stays November thru April. Contact host for details

A scenic view of rolling hills and dense tree cover is captured from the outdoor patio area. Lush green grass and a variety of shrubs provide a natural border, while an expansive sky with scattered clouds completes the tranquil landscape.

Guesthouse in Rapid City

4.91 out of 5 average rating, 689 reviews

Priceless Black Hills View!

No cleaning fees Pool and Rec facilities, seasonal Two Large Furnished Bedrooms w/ new Queen Beds Large living room with new sofa sleeper Newly remodeled bathroom 65'' UHD Smart TV, Dish DVR and Bluray WIFI Highspeed Internet Outdoor patio area with seating Gas grill Pool table and darts Full size fridge/freezer Convection oven Induction cooktop Microwave Keurig coffee and breakfast snacks Washer and dryer Close to Rapid City shopping and dining Nature and wild life Amazing stars out at night!

Top guest favorite

A scenic view showcases the cabin nestled amongst tall pine trees, surrounded by expansive green meadows. A winding gravel driveway leads to the property, with a seasonal pond visible in the foreground, reflecting the clear blue sky.

Home in Hill City

4.99 out of 5 average rating, 254 reviews

Cabin on 20 acres w/ horses, goats, mini donkey

Enjoy country living close to town! Two bedrooms w/ queen size beds and loft w/ queen size pullout sofa allow you to comfortably sleep 6! Just 4 miles from downtown Hill City. Sits on 20 beautiful acres surrounded on 3 sides by Forest Service! Enjoy beautiful surroundings - a seasonal pond outside your cabin (water level varies), horses, mini donkey, mini goats and chickens. Enjoy private setting with the convenience of the owners just 1/4 mile up the driveway to take care of your needs!

Top guest favorite

A geodesic dome structure is situated on a grassy hillside, surrounded by natural scenery. Wooden posts with string lights provide ambient lighting, while gray outdoor seating invites relaxation. The clear sky and distant trees complement the tranquil outdoor setting.

Dome in Hermosa

4.97 out of 5 average rating, 124 reviews

Ponderosa Dome

Furnished with King bed, dual twin beds, coffee-bar, and breakfast table. Private outdoor seating area with lighting, gas and wood fire pit. Wood for purchase. Restroom-guest fav, a few minutes’ walk and located in a shared building, not in unit, pictures in listing. AC in summer (June 1) and electric heater in winter. Non aggressive dogs. No bathroom in unit! Self-check in. Directions are sent the morning of arrival. If your unit requires a passcode, that will be sent upon booking. No WIFI

Top guest favorite

The loft features a cozy sleeping area with a spacious bed dressed in a light blanket. Bright pillows add a pop of color. Natural light fills the room from a large window with red curtains, and a smaller window enhances the airy feel. A decorative feature stands nearby.

4.98 out of 5 average rating, 658 reviews

Harley Court Loft

Cozy loft in the Lead, SD. Moments from downtown, but secluded. Minutes to outdoor activities, skiing, snowshoeing, hiking, biking, or snowmobiling. Winter months, all wheel / 4 wheel drive vehicle is a must!! Close to restaurants, brew pub, and night life!! Kitchenette: microwave, coffee maker, toaster, hot plate, (with pans), and small frig. The loft has electric heat and portable AC. There are 18 steps to get to the loft, for two people. Not kid proof. No pets accepted.

A large lodging building is shown, featuring a combination of wood and stone exterior. The front showcases a spacious deck with wooden railings, surrounded by trees. A garage door is visible on the left side, contributing to the rustic, natural atmosphere of the area.

Guest suite in Keystone

4.75 out of 5 average rating, 386 reviews

Wild, Wild West Experience

On 10 private acres in the heart of the Black Hills, this airbnb offers the best of both worlds—just 8 minutes to Mount Rushmore and 15 minutes to Rapid City. Surrounded by thr National Forest, it’s the perfect home base for exploring the area's sights and scenic drives. After a day of adventure, unwind where you can soak in the views, spot deer wandering through the trees, and enjoy the quiet sounds of nature. It’s the perfect spot to relax, recharge, and plan your next day in the hills.

Top guest favorite

The living area features a modern design with a large flat-screen TV mounted on a textured wall. A vibrant blue retro refrigerator complements the kitchen space, which includes stylish cabinetry and a black countertop. A contemporary electric fireplace adds warmth, while a coffee table sits centrally on the floor.

Guesthouse in Sturgis

4.96 out of 5 average rating, 102 reviews

Hidden Gem in Historic Home

Newly renovated Airbnb duplex, nestled in a quaint small town setting. This charming 400 square foot space is ideal for two people, yet comfortably accommodates up to four with a queen pull-out couch in the living room. Enjoy the convenience of a kitchenette for preparing meals and snacks during your stay. This home is a duplex. The otherside of the duplex is rented out by a young family. Experience the charm of small-town living and book your stay in our inviting Airbnb today!

Top guest favorite

The exterior of the Mercantile features blue siding and a red sign, showcasing a traditional design. A covered porch is present, furnished with a small table and two chairs. Windows allow natural light to fill the space, while trees surround the property, enhancing privacy.

Guesthouse in Deadwood

4.98 out of 5 average rating, 130 reviews

The Mercantile at Mad Peak Lodging, sleeps four

Welcome to the Mercantile at Mad Peak, where mountain old west charm meets modern luxury. This exquisite rental promises an unforgettable getaway in the heart of the breathtaking Black Hills. Nestled among the peaks and valleys of this pristine mountain range, our retreat offers a perfect blend of tranquility, adventure, and relaxation. Whether you're seeking outdoor thrills, cozy nights by the fire, or simply a serene escape, this is your ideal destination.

A covered porch is displayed with two wooden chairs positioned in front. Large glass doors reveal a spacious dining area and kitchen, featuring dark cabinetry and modern appliances. The floor appears polished and reflects the warm lighting from overhead fixtures.

Home in Hill City

4.95 out of 5 average rating, 194 reviews

Hill City Hideaway on the Mickelson Trail

Location, location, location. Hill City is located in the center of the Black Hills and this house is within walking distance of the best parts of Hill City. 40 feet to the world famous Mickelson Trail, 1/2 a block to the 1880s steam train, and 3 blocks to the best restaurant in South Dakota. This home is not too big and not too small. Whether you are doing a couples get away, traveling with kids or your friends this home may be "just right" for you.

Top guest favorite

A wooden cabinet showcases a selection of board games and decorative items. A small table with a plant is situated nearby, creating a welcoming space. Soft lighting emanates from a lamp, illuminating the area and enhancing the cozy atmosphere.

Farm stay in Rapid City

5 out of 5 average rating, 222 reviews

Luxury Ranch Stay

Be our guest on 40 private and fully gated acres. From all windows of the house you can watch 2 horses and cattle grazing through the meadow. The evening sunsets are magical with deer & turkeys wandering through. Relax under the stars at our fire pit (all supplies provided). Let your kids run wild with water guns & a water fall pond to refill at! Located right off HWY 16 makes you only 10 minutes to downtown Rapid City and 20 minutes to Mt. Rushmore!

The cabin interior features natural wood paneling, creating a warm environment. A queen bed is displayed with neatly arranged linens, alongside a set of twin bunk beds. A wooden chair and a small desk are visible, with a map of Hill City adorning the wall.

Cabin in Hill City

4.86 out of 5 average rating, 195 reviews

Hip Hill City Cabin near Mt. Rushmore

Rustic pine sleeper cabin in the beautiful Black Hills. One queen bed with twin bunk beds (three beds in total). Cabins do not include a shower, bathroom or running water inside. Showers and bathrooms are available for free use in main guest shower house. A great base for touring the area, with quick access to lakes, Mickelson Trail and a 20 minute drive to Mt. Rushmore. Featuring an award-winning bistro, wine and beer tasting room.

Vacation rentals for every style

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Convenient locations with everyday essentials

Popular amenities for West Pennington family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Top guest favorite

A comfortable living area is presented with two dark leather sofas and an accent ottoman. A ceiling fan is visible above, enhancing airflow. The walls feature light wood paneling and a large framed image of a mountain monument. A small dining area with high stools and shelves can also be seen.

Home in Rapid City

4.97 out of 5 average rating, 106 reviews

Monumental Stay-HOT TUB/lower unit/SUPER CLEAN

The interior of the tiny house features wood-paneled walls and an exposed beam ceiling. A comfortable day bed with decorative pillows is positioned against the wall. A small dining area is situated nearby with four bar stools, while a television is mounted for entertainment.

Tiny home in Spearfish

4.92 out of 5 average rating, 217 reviews

Tiny Timber- Stunning Tiny House

A charming home is framed by towering trees, with a welcoming entryway featuring a large front porch. Stone steps lead up to the door, while colorful flower beds enhance the outdoor space.

Cabin in Rapid City

4.95 out of 5 average rating, 577 reviews

Hideaway on Bridge Lane

A charming house surrounded by trees is highlighted by a wooden deck with planters and steps leading up to it. The front entrance features large windows that provide views of the outdoors, while vibrant yellow flowers add a splash of color to the garden area.

4.87 out of 5 average rating, 233 reviews

Reato House--Cozy comfort away from home, HOT TUB!

A modern kitchen space is highlighted by a large island with seating for four. Sleek black appliances, including a vintage-style refrigerator, complement the white cabinetry and tile backsplash. Natural light fills the area through overhead lighting and nearby windows, enhancing its contemporary design.

Home in Spearfish

4.93 out of 5 average rating, 271 reviews

Modern 2-Bedroom Getaway

A peaceful outdoor patio area features two comfortable chairs positioned to take in scenic views of the surrounding greenery and hills. The patio is surrounded by lush foliage, providing a natural backdrop for relaxation.

Guest suite in Spearfish

4.89 out of 5 average rating, 150 reviews

Guest Suite with Beautiful Views and Hot Tub

Top guest favorite

The exterior of the cabin showcases a combination of natural wood siding and green accents, framed by tall trees. A welcoming deck extends from the front entrance, and landscaped stone beds add charm. The adjacent structure features a garage and earthy tones, integrating seamlessly with the surroundings.

Cabin in Black Hawk

4.99 out of 5 average rating, 278 reviews

Squirrel Hill Cabin - hot tub, gameroom, wi-fi

A wooden deck overlooks a serene creek, surrounded by lush greenery and colorful foliage. Two comfortable chairs and a small table are positioned for outdoor relaxation, with a backdrop of gently sloping hills and trees, enhancing the peaceful atmosphere of the setting.

Cabin in Rapid City

4.82 out of 5 average rating, 352 reviews

Amazing Creek-side Cabin

Family- and pet-friendly home rentals

Top guest favorite

A spacious cabin is set amidst tall trees, featuring a welcoming porch with ample seating. A gravel driveway leads up to the cabin, which is flanked by greenery. A fire-pit area is visible to the left, complemented by a blue storage container.

Cabin in Deadwood

4.96 out of 5 average rating, 117 reviews

Darby's Cabin in the Woods

An outdoor seating area is showcased, featuring four wicker chairs arranged around a circular stone firepit. A wooden bench is positioned nearby, surrounded by lush green grass and natural foliage. A wooden fence adds privacy to the space.

Cabin in Rapid City

4.94 out of 5 average rating, 143 reviews

❖Charming Log Cabin❖Firepit❖Great Deck with Grill❖

A spacious mobile home is situated in a winter landscape, surrounded by tall pine trees. Snow blankets the yard, with a wooden staircase leading up to the front entrance. Large windows provide views into the home, enhancing the serene setting.

Home in Hill City

4.93 out of 5 average rating, 41 reviews

Western Pines

The home features a single-story brick façade with a well-maintained front yard. A two-car garage is visible on the right, while large windows provide glimpses of the interior. The driveway leads up to the house, bordered by a neat gravel edge.

Home in Rapid City

4.82 out of 5 average rating, 104 reviews

Pool, deck, fire pit, and trampoline!!!

Top guest favorite

A cozy living space is highlighted by a leather sofa and an ottoman, accompanied by a wooden dining table. Natural light filters through multiple windows with white blinds, illuminating bookshelves and decorative art on the walls. A ceiling fan and an air conditioning unit are visible.

4.94 out of 5 average rating, 210 reviews

Downtown Loft

Top guest favorite

The exterior of the house is showcased, featuring a front yard with manicured grass and landscaping. A gravel pathway leads to the entrance, framed by trees and bushes. A garage is visible in the background, providing additional parking space.

Home in Rapid City

4.91 out of 5 average rating, 332 reviews

Rapid City Black Hills Westside Home 2

Top guest favorite

The exterior of a contemporary studio showcases natural wood siding complemented by sleek, metal accents. Large glass doors provide a view into the interior, while warm lighting illuminates the structure. A comfortable rocking chair is positioned on the porch, enhancing the inviting outdoor space.

Tiny home in Rapid City

4.98 out of 5 average rating, 251 reviews

Bale & Butterfly Bungalow

A bright sitting area is furnished with two upholstered armchairs and a wooden side table, complemented by natural light from a corner window. A decorative lamp and framed artwork enhance the inviting space. A door leads to an outdoor area, surrounded by greenery.

Loft in Rapid City

4.88 out of 5 average rating, 112 reviews

Cozy Apartment in Rapid City

Family-friendly home rentals with a pool

A modern living and dining area features a comfortable sofa with decorative cushions and a coffee table placed in front. A spacious dining table with six chairs occupies the center, surrounded by large windows that allow natural light to brighten the space.

4.86 out of 5 average rating, 36 reviews

Jackalope Loft in Downtown Custer, Sleeps 6

Top guest favorite

A modern cabin with a sloped roof and wooden deck is surrounded by lush greenery. Vibrant wildflowers add color to the scene, while tall pine trees frame the structure. A welcoming sign is visible nearby, enhancing the cabin's rustic charm.

4.97 out of 5 average rating, 92 reviews

Moonlight Pines-Happy Little Cabin

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

Guesthouse in Rapid City

4.9 out of 5 average rating, 191 reviews

Gayle's Cottage

A private guest suite features a spacious bed with a textured gray blanket. A small round table and two chairs offer a cozy seating area. A flat-screen television is mounted on the wall, and a compact kitchenette is positioned beside a bathroom door. Natural light enters through the window with dark curtains.

Guest suite in Rapid City

4.85 out of 5 average rating, 40 reviews

Red Rock Private Guest Suite

Top guest favorite

A private indoor pool features a vibrant blue surface, with a shallow entry area marked with depth indicators. Large windows allow natural light to fill the space, while lounge chairs are positioned along the edges for relaxation. The pool area is designed for guest privacy.

Home in Rapid City

5 out of 5 average rating, 139 reviews

Private Pool! Great Rapid City Location!

A rustic cabin is shown with wooden siding and a green roof. The front porch features two rocking chairs, providing a relaxing spot to enjoy the outdoors. The cabin sits on a gravel area, with grassy surroundings and rolling hills visible in the background.

Cabin in Piedmont

4.82 out of 5 average rating, 438 reviews

Rustic Cabin

A comfortable living area features a brown leather sofa adorned with patterned cushions. Above it, woven wall art is displayed, accompanied by hanging pendant lights. A rustic wooden ladder leans against the wall, and small side tables sit beside the sofa.

5 out of 5 average rating, 88 reviews

Condo Across from Terry Peak*Hot tub*Spacious

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