Family-friendly holiday rentals in Keystone

A spacious home is nestled among tall trees, overlooking a gently flowing creek. The property features a large deck and stonework, blending harmoniously with the natural surroundings, while vibrant greenery enhances the serene environment.

4.98 out of 5 average rating, 128 reviews

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.

4.93 out of 5 average rating, 135 reviews

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

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

4.99 out of 5 average rating, 195 reviews

A dining area features a white table surrounded by blue chairs, inviting shared meals. A cozy seating area with a brown sofa and a patterned rug complements the space. Natural light flows through large windows adorned with light curtains, enhancing the room's welcoming feel.

Bungalow in Custer

The Jasper House: A cheerful downtown bungalow

Named after a local gemstone, The Jasper House is a stylish, centrally-located 1940s bungalow that was newly remodeled in 2022. This cheerful 2-bedroom house sleeps 4 and offers a full kitchen, full bath, fenced back yard with fire pit & grill, and more! -Five minute walk to downtown shopping, award winning restaurants & the Mickelson Trail -Ten minute drive to Custer State Park; twenty minute drives to both Jewel Cave National Monument & Wind Cave National Park -One block from the city pool

4.99 out of 5 average rating, 294 reviews

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

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!

4.97 out of 5 average rating, 144 reviews

Cabin in Keystone

The Winsome Cabin - Hinterwood Inn & Cabins

The Winsome Cabin is part of Hinterwood Inn & Cabins, situated 60 ft. from National Forest. Enjoy hiking and wildlife sightings from your front door! The cabin has 2 bedrooms, each with a queen bed, a queen murphy bed in the living room, a bathroom with a shower (no tub), and an apartment size kitchen w/ essentials. Custom built by the owners, enjoy the beautiful stump accent wall, vaulted ceilings, and large windows. Includes a private deck with a gas grill, private fire pit area, and more!

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.

4.99 out of 5 average rating, 184 reviews

Private Pool! Great Rapid City Location!

*Please be sure to read all house information! Welcome to Mary Jo's Place, a charming 1950s Rapid City home! Sleeping six with two bedrooms and two bathrooms. Located near the Historic West Boulevard in the center of Rapid City! A great location with nearby parks, walking and hiking trails, grocery, and restaurants. Also, easily access Mount Rushmore Road and Interstate 90. This home has recently been updated and is ready for your stay! Did we mention there is a private heated indoor pool!

4.77 out of 5 average rating, 430 reviews

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

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.

4.88 out of 5 average rating, 143 reviews

Home in Keystone

Rock Lodge covered parking and Private Hot Tub!

Relax with the whole family at this peaceful, fully renovated lodge nestled among the pines in Keystone. This stylish 4-bedroom home offers the perfect blend of rustic charm and modern comfort. Enjoy premium amenities including a hot tub, fire pit, and spacious backyard. Perfectly located in a quiet residential area, you are just steps from downtown and minutes away from the iconic sights of the Black Hills, making it the ideal base for your next mountain adventure.

4.96 out of 5 average rating, 219 reviews

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

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.

4.83 out of 5 average rating, 398 reviews

A charming creek-side home is featured, showcasing rustic wooden siding and a welcoming entrance. A pathway leads to a wooden deck, with a flagpole prominently displaying the American flag. Vibrant green grass and a fire pit with red chairs enrich the outdoor space, surrounded by natural hills.

Cabin in Rapid City

Creek-side Cabin | Hot Tub + Trout Fishing

Wake up to the sound of a babbling creek, sip your morning coffee on the deck while bighorn sheep graze on the hillside, and spend your evenings soaking in the hot tub under a sky full of stars. This beautifully furnished 3-bedroom Black Hills cabin sits right on the water — perfect for trout fishing, family gatherings, romantic getaways, or simply unplugging from the world. With stunning creek and mountain views, This is a Complete Black Hills retreat.

4.99 out of 5 average rating, 216 reviews

The A-frame cabin is framed by tall pine trees, showcasing a blend of wood and metal in its exterior design. Warm lights illuminate the structure, highlighting the large windows and inviting entrance. A stairway leads to the deck, enhancing accessibility to the cozy retreat.

Tiny home in Custer

Modern A-Frame Cabin Next to Custer State Park

Enjoy this spacious modern A-Frame Cabin. Located just 5 minutes to Custer State Park. Experience views of the Needles Highway and Black Elk Peak while you drink your morning coffee! You will have access to the entire house all to yourself! Great area to hike, bike, see the fluffy buffalo. Just a two minute drive to downtown Custer. This area has great ATV and kayak, trail ride rentals near by! Feel refreshed when you stay in this rustic gem.

4.96 out of 5 average rating, 158 reviews

Executive Golf Course Home, Family Friendly

Quiet stay in an exclusive golf course neighborhood entering the Black Hills - 30 minutes to Mount Rushmore, 20 mins to Sheridan Lake, while being a quick 10 mins to Walmart Supercenter or 12 minutes to downtown Rapid City. Easy access to Black Hills and Badlands National Park attractions. Senior and Active Military Discounts available - must be person making reservation and be willing to provide proof of ID at time of booking.

Popular amenities for Keystone family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 193 reviews

A private hot tub is situated on a covered patio, surrounded by lush greenery. The calming waters reflect the natural light filtering through the canopy of trees. Nearby, a wooden bench and a swing add to the serene outdoor setting.

Cabin in Custer

Tenderfoot Creek Retreat

5.0 out of 5 average rating, 100 reviews

A wooden deck features a modern hanging swing chair, complemented by a lush green potted plant. Large windows provide a view into the interior, and a bold red front door adds a striking focal point to the entrance.

Villa in Custer

Contemporary retreat with BEST location in Custer.

4.93 out of 5 average rating, 145 reviews

Castle in the Sky

Guest suite in Rapid City

A spacious bedroom features a comfortable bed with a dark headboard, framed by two sleek nightstands. Wall-mounted sconces provide soft lighting, and large windows offer views of the outdoors. Light wood accents create a warm ambiance, complemented by a decorative wall art piece.

Private and peaceful. Hot tub and scenic views.

4.99 out of 5 average rating, 332 reviews

4.91 out of 5 average rating, 111 reviews

The exterior of a cozy cabin is illuminated by soft outdoor lighting. A hot tub sits on the deck alongside a fire pit, both enhancing the tranquil setting. A grill is positioned nearby, and the cabin's large windows reflect warm indoor lighting, inviting a sense of comfort.

Home in Lead

Lead/Deadwood, Pet friendly. Central location

4.99 out of 5 average rating, 254 reviews

A single-story house is depicted with a wooden exterior in a soft grey shade. Large glass sliding doors offer views of the interior, framed by two side windows. A small seating area with two chairs is visible on the porch, surrounded by grassy grounds and pine trees.

Cottage in Hill City

Mystic Road Cottage… -Peaceful -Private -Hot tub

4.98 out of 5 average rating, 185 reviews

A modern tiny cabin features reflective walls, blending into the surrounding nature. Tall trees and a blue sky are mirrored on the surface, creating a seamless connection with the forest. The cabin's structure is set among rocky terrain, emphasizing its unique design.

Tiny home in Lead

Mirror Cabin in the Black Hills

4.98 out of 5 average rating, 137 reviews

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.

Cabin in Lead

Moonlight Pines-Happy Little Cabin

Family- and pet-friendly home rentals

4.85 out of 5 average rating, 180 reviews

A view shows several rustic cabins arranged around a grassy area, surrounded by trees. A sign indicates pony rides nearby. Fencing encloses the site, enhancing a sense of openness. The horizon features gently rolling hills, contributing to the serene setting.

Cabin in Hill City

High Country Guest Ranch - #25 Rodeo

Guest house in Rapid City

The game room features a classic wooden pool table with a blue felt surface, surrounded by a carpeted floor. A wall of brick showcases various framed memorabilia and decorative items, enhancing the recreational atmosphere. Two high-top chairs are positioned nearby.

Priceless Black Hills View!

4.91 out of 5 average rating, 749 reviews

4.94 out of 5 average rating, 133 reviews

A charming exterior of a cottage is framed by lush green grass and trees. The yellow door stands out against the muted tones of the building, inviting guests inside. A split rail fence is visible in the foreground, completing the rustic countryside feel.

Guest house in Hermosa

Black Hills Bungalow

4.95 out of 5 average rating, 208 reviews

Cabin in Custer

Black Hills Custer:AC+DirecTV+Wi-Fi+Washer/Dryer

4.98 out of 5 average rating, 171 reviews

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.

Guest house in Deadwood

The Mercantile at Mad Peak Lodging, sleeps four

Guest suite in Rapid City

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.

Quiet private suite with garage bay & kitchenette

4.98 out of 5 average rating, 545 reviews

A well-kept single-story house is framed by lush green grass and young trees. The entrance features a covered porch and a decorative lattice, providing a welcoming view. Windows allow natural light to enter the interior, while a pop of color is added by a blue trash bin nearby.

4.96 out of 5 average rating, 278 reviews

Perfect for families and business travelers!

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.

4.82 out of 5 average rating, 130 reviews

Pool, deck, fire pit, and trampoline!

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 130 reviews

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.

Apartment in Lead

Condo Across from Terry Peak*Hot tub*Spacious

4.95 out of 5 average rating, 104 reviews

An aerial view of a spacious living area showcases large windows that invite natural light, framed by a rustic stone accent wall. A modern fireplace is positioned beside a comfortable seating arrangement, with a dining table visible nearby, emphasizing an open layout.

Cabin in Lead

Huge Windows! Modern Powderhouse Pass Home

Superhost

Home in Keystone

Cozy Keystone Cabin with Hot Tub

4.57 out of 5 average rating, 96 reviews

Superhost

The entrance to the treehouse is flanked by large stone formations, leading up a set of wooden steps to the main door. Soft lighting highlights the cabin's rustic architecture, surrounded by tall pine trees and lush green grass under a sunset sky.

Treehouse in Custer

Black Hills Gold RushTreehouse with Mountain View

4.82 out of 5 average rating, 77 reviews

4.86 out of 5 average rating, 44 reviews

Cabin in Rapid City

10 Person Cabin near Mount Rushmore

4.92 out of 5 average rating, 62 reviews

Home in Lead

New, 6 King Beds, 5 .5 Bath, Home Theater, Hot Tub

4.89 out of 5 average rating, 9 reviews

Home in Custer

Mickelson Trail Lodge 5 acres of privacy in Custer