
Family-friendly holiday rentals in Pennington County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Pennington County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Farm♡tastic stay @ Hills Roost Farm!
Our farm's only bnb, "The Roost," offers a clean, modern, & fun space to stay. Located in the lower walkout level of our home, it's similar to a suite. Offering 575 sq. ft. of private, clean, well maintained living quarters include, a kitchen, a cozy living space, w/twin sofa bed, & a spacious bed & bathroom. Chickens just outside your door to greet you a "rise & shine" morning & flowers everywhere. Our seasonal gardens are open for you to enjoy picking organic food, along with farm fresh eggs.

Welcome to Case Place! A spacious quiet retreat!
Welcome! This relaxing & unique a space sets the stage for beautiful views of the Black Hills & gorgeous sunrises & sunsets right from the hot tub! Case Place is 15 minutes from Rapid City and 30-40 minutes from Mt. Rushmore, Custer & Keystone, & Sturgis. Box Elder is growing & a has public golf course, Ellsworth Air Force Base/Museum! Guests often take in the unique experience of seeing & hearing the sound of freedom from the majestic B-1's! Honeymooners /Anniversaries ❤️ Inquire w/ options.

Restored Nemo Farmhouse on Centennial Trail W WiFi
Bring your ATV'S! Plenty of parking. On the Centennial Trail system. Fast wifi, smart TV with Dish channels. We are about 20 minutes from Sturgis, half an hour from Deadwood, and 40 minutes from Rapid City. The nighttime sky is very dark for viewing all the constellations; we have solar lights around the house, but it can be dark without a flashlight. Please keep in mind we are in the forest, and there are bugs, flying insects, and small critters. We work very hard to keep them out of the house!

Squirrel Hill Cabin - hot tub, gameroom, wi-fi
A hidden gem in the heart of the Black Hills, our cabin is nestled on 3 private acres lovingly named Squirrel Hill. With decks in every direction, you're encouraged to take in the abundance of nature. Watch for deer, turkey, birds and squirrels. Relax under the pines in the hot tub or on the deck featuring a gas firepit and 10-person table. Inside, you'll find everything you need for a well-appointed getaway. Worlds away from the hustle & bustle of real life; just 10 minutes west of Rapid City.

Creekside Sanctuary
Creekside Sanctuary is a 6+ acre paradise for families, friends, celebrations or retreats. Naming this property was not easy, not only is this a Sanctuary for relaxation and rejuvenation, guests can also enjoy the popular site seeing and abundant wildlife native to our beautiful Black Hills. Whether winter or summer, there are activates nearby - fishing, hiking, skiing, snowmobiling, ice skating. The large yard is host to deer and turkey, an ideal gathering spot for celebration, fun and games.

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.

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!

Clean, one-level living close to amenities!
-No recent reviews due to longer-term tenant- **New 12” memory foam mattress on queen bed!** **After multiple guest’s suggestions, I’ve replaced the living room sofa bed and kitchen stools & added a chair to the living room space!** Less than 2 miles from downtown Rapid City! Walking distance to hospital & other amenities. Newly remodeled one bedroom, one bath home with driveway & off-street parking. Large deck with patio furniture. Window A/C unit in kitchen during spring/summer months.

Pet friendly 2 bedroom log cabin with hot tub.
This beautiful large 2 bedroom cabin nestled right outside of Sturgis SD can comfortably accommodate several guests, as it has 2 bedrooms as well as 2 living rooms. One of the living rooms has 2 fold out twin beds. 7 person hot tub! patio furniture as well. This cabin gives you the privacy you need yet the comforts of being 5 mins from a grocery store. Gorgeous views of the Black Hills. Fully furnished home. BBQ grill. We have a few different airbnbs and the cabin is completely private.

The Gemstone
This wonderful home is located in Rapid City. Come sit relax and enjoy very comfortable reclining leather sectional. Enjoy a 85 inch tv in the basement with a reclining sofa and a wet bar. Very close to Rushmore mall and the interstate. Great place if you’re wanting to travel to all the beautiful places the Black Hills has to offer. Only 20 minutes to the beautiful city of keystone where Mount Rushmore is located. It’s only 30 minutes to the Sturgis Bike Rally and much much more.

Castle in the Sky
Are you looking for a luxurious, unique place to stay? This house sits overlooking Rapid City with incredible skyline views, every evening is as picture perfect as the glowing city lights. This unique house is a fun mix of eclectic and fancy. Originally built as a local builder's "Coup de Grande", he ended up only finishing the guest house. You will find high-end finishes mixed with eclectic choices. We promise this will be one of the most memorable places you'll ever stay!

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!
Popular amenities for Pennington County family-friendly rentals
Family-friendly home rentals with a hot tub

Monumental Stay-HOT TUB/Garden Level/SUPER CLEAN

Modern 5-bed cabin with Hot Tub, King size beds

Lazy L Lodge

Luxury Escape w/Hot Tub, Firepit and Barrel Sauna

Jägerhaus - Mountain Lodge on Private Estate

Chalet Mt Rushmore VIEWS Hot Tub

Steel Pines Cabin on Maitland rd.

Tenderfoot Creek Retreat
Family- and pet-friendly home rentals

Perfect for families and business travelers!

Ponderosa City Council

Grandma's House in the Heart of the Black Hills

The Rock and Block house

Priceless Black Hills View!

Black Hills Rambler-Tiny House

Falsebottom Hide-away

âś¶Canyon Lakeâś¶PingPongâś¶Golf Course Closeâś¶Garageâś¶
Family-friendly home rentals with a pool

Cozy Black Hills Escape near Rushmore

Moonlight Pines-Happy Little Cabin

Mineral Mountain Lodge in Gilded Mountain

Private Pool! Great Rapid City Location!

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

Timber Trails: Pet-Friendly Haven for Adventurers

High Country Guest Ranch - #25 Rodeo

Rustic Cabin
Destinations to explore
- Rentals with outdoor seating Pennington County
- Rentals with a fireplace Pennington County
- Fitness-friendly rentals Pennington County
- Rentals with a hot tub Pennington County
- Boutique hotels Pennington County
- Cabin rentals Pennington County
- Farm stay rentals Pennington County
- House rentals Pennington County
- Motorhome rentals Pennington County
- Rentals with a kayak Pennington County
- Bed and breakfasts Pennington County
- Rentals with a patio Pennington County
- Rentals with an accessible-height toilet Pennington County
- Rentals with lake access Pennington County
- Loft rentals Pennington County
- Tent rentals Pennington County
- Tiny house rentals Pennington County
- Rentals with breakfast Pennington County
- Campsite rentals Pennington County
- Private suite rentals Pennington County
- Apartment rentals Pennington County
- Ski-in/ski-out rentals Pennington County
- Chalet rentals Pennington County
- Guest house rentals Pennington County
- Flat rentals Pennington County
- Rentals with a firepit Pennington County
- Pet-friendly rentals Pennington County
- Rentals with a washing machine and dryer Pennington County
- Townhouse rentals Pennington County
- Cottage rentals Pennington County
- Rentals with pools Pennington County
- Hotel rooms Pennington County
- Family-friendly rentals South Dakota
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