
Holiday rentals with a pool in Pennington County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pennington County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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!

Red Rock Private One Bedroom Apartment
Enjoy your stay in the beautiful Black Hills in our fully furnished, private one bedroom apartment! Comfortable queen size bed with fresh linens, blankets, & pillows. Tub & shower and full size washer and dryer in the bathroom. Kitchen has a full size refrigerator, flat top electric stove, built-in microwave, & dishwasher! Plates, cups, silverware, pots, pans, & cooking utensils are also available for your use. Living room has TV, full size pull- out bed in couch, & bar area for dining.

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!

Condo Across from Terry Peak*Hot tub*Spacious
Welcome to Story Blu Summit, a newly updated 2BR/2Bath condo within steps of Terry Peak and the use of all the amenities Barefoot Resort. ★ Located across from Terry Peak Ski Hill ★ Gorgeous Views ★ 6 miles to Deadwood, SD ★Minutes to downtown Lead ★ Ski, hike, bike, snowmobile trails all close by ★ Large Smart TV's in each bedroom ★ King Bed in Master ★ High-speed internet ★Remote work friendly ★ Use of communal private Hot Tub x3, heated indoor pools x2, exercise room and sauna

Pool, deck, fire pit, and trampoline!!!
Beautiful home in a residential neighborhood on the West Side of Rapid City. Perfect for families and gatherings. You will have access to a two car garage, above ground pool, trampoline, large outdoor deck, fire pit, and a grill that’s available when the weather permits. The house is almost 80 years old and there are some features that are still from the 50s and we like those. We don't plan on changing them so if you're looking for a totally updated house this house might not be for you.

Views of Mt Rushmore, Private Hot Tub!
"The Jefferson" is a private cabin set in the pines where guests will be embraced by the natural beauty of the Black Hills. Centrally located, this home has easy access Hill City, Custer State Park, Crazy Horse and all the best Hills activities. Featuring 2 Bedrooms, 2 baths, 2 living areas, kitchen, large wraparound deck, bbq grill, fire pit and patio. Both levels have views of Mt Rushmore! Enjoy the heated pool at Ramada or escape to your own private hot tub after a day of exploring.

Crescent Moon Retreat
Welcome to Crescent Moon Retreat! Escape to this spacious and stylish 5-bedroom, 3.5-bath getaway designed with families and groups in mind. From the open-concept living space to the fully stocked kitchen, every corner is made for comfort and connection. Unwind around the cozy fire pit, soak in the outdoor hot tub under a blanket of stars, or enjoy access to the nearby clubhouse featuring a year-round heated pool, a seasonal outdoor pool, and a splash zone just for the kids.

Kindred Pines At Terry Peak
Welcome to Kindred Pines. A charming Black Hills Condo, privately owned, just steps away from the slopes of Terry Peak Ski Area, nestled in a town rich in history & surrounded by so much natural beauty. Our condo is perfectly situated for outdoor adventure and cozy relaxation. In the winter, enjoy some of the best skiing and snowboarding in the region. When the snow melts, the Black Hills transforms in to a haven for hiking, biking and exploring iconic landmarks.

Moonlight Pines-Happy Little Cabin
Moonlight Pines (n.) a place where memories are made. Hello, we are so happy you’re here! Relax, unwind, + consume all the beauty + positive energy our space offers. Steps away from trails + slopes, have fun exploring our beautiful backyard knowing a cozy fire, a game of backgammon, a glass of wine, + a soak in the hot tub await (#hygge)! Connect with the peacefulness of nature and, of course, enjoy the moonlight shining down on all the pines!

The Oak Grove Cabin
Welcome to the Oak Grove Cabin. This 3 bedroom/2 bath cabin is set apart and surrounded by oak trees. With multiple gathering areas there's enough room for the whole family to be together. Take a deep breath of fresh air and listen to the water run down the stream on this 8 acre property surrounded by National Forest. You will feel complete peace while also being minutes away from Mt Rushmore (2.4 miles) and Custer State Park (15 mins)

1BR Retreat | Pool, Gym & Hiking
Welcome to your perfect getaway in the heart of the Black Hills! Whether you're here for adventure, relaxation, or a little of both, our beautiful 1-bedroom, 1-bathroom apartment offers the ideal home base for your stay. With access to premium amenities like an outdoor pool, fully equipped gym, and private hiking paths, you'll have everything you need to unwind and explore.

Gayle's Cottage
This cozy place is nestled in the black hills with wonderful views! You will love our place because this is a wonderful and quaint guest house located at the foot of the black hills. Enjoy the deer and turkeys footsteps from your front door that visit the property daily. My place is great for couples, solo adventurers, business travelers, and families with kids.
Popular amenities for Pennington County rentals with a pool
House rentals with a pool

Spacious 5 Bed 4 Bath, Hot Tub, Arcade, Paved Road

Legends Lodge

Cozy T Cabin at Powderhouse Pass

The Sweet Life

Blackhorn-Lodge

Valley Vista Retreat - New 5BR Cabin

Kickback Shack, Black Hills, Ski, UTV Parking+

Midnight Star
Apartment rentals with a pool

Remodeled Condo at Terry Peak SD

Roomy Condo on the Mountain

B4 rustic lodge feel 1bd/1ba, walk to ski, w/ pool

A3- Spacious 2bd/2ba condo w/ hot tub, walk to ski

B2- classic ski vibe 1bd/1ba, walk to ski, w/ pool

A8- Bright lodge feel 1bd/1ba walk to ski, w/ view

B3 classy updated 1bd/1ba, walk to ski, w/ pool

B12 Original woodsy 2bd/2ba, walk to ski, hot tubs
Other holiday rentals with a pool

Mountains & Mimosas

Mountain View Suite near Mount Rushmore in the Bla

Jackalope Loft in Downtown Custer, Sleeps 6

Red Rock Private Guest Suite

The Miner's Cabin

Cozy Keystone Cabin with Hot Tub

The Golden Slipper Cabin

The Ingersol Mine Cabin
Destinations to explore
- Rentals with a fireplace Pennington County
- Rentals with a washing machine and dryer Pennington County
- Rentals with lake access Pennington County
- Apartment rentals Pennington County
- Rentals with breakfast Pennington County
- Fitness-friendly rentals Pennington County
- House rentals Pennington County
- Motorhome rentals Pennington County
- Tiny house rentals Pennington County
- Rentals with a kayak Pennington County
- Bed and breakfasts Pennington County
- Rentals with a patio Pennington County
- Family-friendly rentals Pennington County
- Rentals with a hot tub Pennington County
- Cottage rentals Pennington County
- Pet-friendly rentals Pennington County
- Cabin rentals Pennington County
- Rentals with outdoor seating Pennington County
- Loft rentals Pennington County
- Chalet rentals Pennington County
- Private suite rentals Pennington County
- Rentals with an accessible-height toilet Pennington County
- Hotel rentals Pennington County
- Farm stay rentals Pennington County
- Flat rentals Pennington County
- Rentals with a firepit Pennington County
- Rentals with pools South Dakota
- Rentals with pools United States