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Vacation 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.

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Home in Lead

4.83 out of 5 average rating, 6 reviews

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

The whole group will be comfortable in this spacious and unique space. Welcome to "This is Livin'," an extraordinary six-bedroom, 5.5 bath vacation home in the Powder House Pass Development of the northern Black Hills, South Dakota. With sleeping arrangements up to 22 people. This haven of opulence offers an unparalleled experience, ensuring that your stay is nothing short of exceptional. Upon entering, you are greeted by a meticulously designed interior that radiates comfort and sophistication

Home in Hill City

4.67 out of 5 average rating, 30 reviews

Black Hills Cabin - Stony Ridge

The Stony Ridge is a great home in the town of Hill City. Guests love the fact that they can walk downtown to enjoy the restaurants, shops and galleries. The three bedrooms in the home each have a queen sized bed and the two baths are fully furnished. The living room is comfortable and the kitchen fully furnished along with a gas grill outside. You are also invited to enjoy to pool and hot tub across the street at the Super 8 motel and come out and pet the horses at the Double Diamond Ranch.

Home in Rapid City

4.75 out of 5 average rating, 8 reviews

Spacious & Accommodating with Great View!

Wake up to an amazing view of the Black Hills in this spacious 4 bedroom 3 bath, 2-level home with full garage. With enough room for everyone, you will have your own space and be very comfortable. The scenic drive to Sturgis on Scenic Nemo Road is only 45 minutes. The community outdoor pool and Rec area is available from Memorial Day to Labor Day for you to enjoy. The property is 15 minutes to Downtown Rapid City also close to Mount Rushmore, Custer State Park, Pactola Lake, and Hill City.

Home in Rapid City

4.92 out of 5 average rating, 73 reviews

lNDOOR POOL! The FUN house

Are you ready to have a FUN vacation?! This house boasts 7,000 sq. ft. of every amenity you could dream of! Everyone in the family will be glad you picked this home. Not only does it have all the amenities but it has a decreased carbon footprint thanks to the solar panels that power the house! This property is not pet friendly. *No smoking allowed on property* -INDOOR POOL with Water Slide and 10-Person Hot Tub! -Sauna -Weight Room -Pool Table, Air Hockey, Foosball -Outdoor Volleyball Court

Cabin in Lead

4.95 out of 5 average rating, 22 reviews

Timeless-Trailer Parking,Pool, ATV- Snowmobile

Have fun with the whole family at Timeless Lodge of the Black Hills. This build is just completed with 5 king bedrooms- all own bath, a bonus bedroom-kids area with 4 twins, and 2 y kids fold outs- their own bath. Bonus room is complete with ping pong, Foosball, age variety of toys and books. The lower level set up for game days a 4 screen split TV, recliners, sectional, wall bean bag, game table, and more to come. Access to club house; 2 pools, splash pad, pool table, shuffle board-more

Home in Lead

4.96 out of 5 average rating, 23 reviews

Welcome to Knotty Hideaway

Knotty Hideaway itself boasts an amazing open floor plan perfect for entertaining with the living, kitchen, and dining rooms all connected. Enjoy the covered patio right off the kitchen which consists of a gas fire pit to relax and enjoy. This home is located next to Mickelson Trails and Trail Head #5 Snowmobile Trail. Just a few minutes from Terry Peak Ski Resort and Lead/Deadwood. Enjoy the oversized 2 car garage for the toys. Full access to clubhouse and pools. Come stay, relax and enjoy.

Home in Rapid City

4.83 out of 5 average rating, 92 reviews

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.

Home in Lead

5 out of 5 average rating, 26 reviews

Serenity Now

Enjoy the Serenity of the Black Hills in this spacious, custom built 6 bedroom 5.5 bathroom home that sleeps 20 people. Designed with you in mind and furnished with all the essentials to ensure a relaxing retreat. Nestled in the northern Black Hills of South Dakota, Powder House Pass has direct access to state Snowmobile Trails and close proximity to ATV trails. In addition, there is access to the Nationally Recognized Mickelson Trail with 110 miles of walking and biking trails.

Home in Rapid City

5 out of 5 average rating, 108 reviews

Private Pool! Great Rapid City Location!

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!

Cabin in Lead

4.92 out of 5 average rating, 38 reviews

Welcome to Iron Horse Cabin

Located near Terry Peak & Deadwood.Quiet ATV/UTV friendly community located on a paved road with parking for up to 3 trucks with 3 trailers or 6 vehicles. The Iron Horse Cabin is in the Gilded Mountain Community & in additional to a private hot tub, Guests have access to a shared salt water pool (heated year-round!), 2 additional hot tubs, exercise room, pool table, sauna & a large space for gatherings at the Community's Clubhouse.

Home in Lead

5 out of 5 average rating, 6 reviews

Cozy T Cabin at Powderhouse Pass

Welcome to your luxury retreat in Powderhouse Pass! Cozy T Cabin is a brand new home built with luxury and relaxation in mind! Enjoy all of the modern luxuries of this home, in addition to a large wrap around deck, a private patio with a hot tub, and the year round heated pool at the community club house! Built in 2023, no detail was overlooked in the design and build of this incredible home!

Guesthouse in Rapid City

4.9 out of 5 average rating, 191 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Pennington County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Lead

5 out of 5 average rating, 27 reviews

Crescent Moon Retreat

Home in Lead

4.9 out of 5 average rating, 29 reviews

Blackwoods Retreat in Powder House Pass w/Hot tub

Home in Lead

4.96 out of 5 average rating, 27 reviews

Timber Trails: Pet-Friendly Haven for Adventurers

Home in Custer

5 out of 5 average rating, 14 reviews

Dwntwn Custer Farmhouse on Main St. with Hot Tub

Home in Lead

4.9 out of 5 average rating, 29 reviews

Kickback Shack, Powderhouse Pass, Black Hills, SD

Home in Lead

4.91 out of 5 average rating, 35 reviews

Valley Vista Retreat - New 5BR Cabin

Home in Box Elder

4.94 out of 5 average rating, 33 reviews

Summer Swimming Retreat

Home in Custer

4.79 out of 5 average rating, 24 reviews

Wind Dance Lodge w/ HOT TUB Large Shop garage

Condo rentals with a pool

Condo in Lead

New place to stay

Remodeled Condo at Terry Peak SD

Condo in Lead

4.89 out of 5 average rating, 57 reviews

Roomy Condo on the Mountain

Condo in Lead

5 out of 5 average rating, 3 reviews

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

Condo in Lead

4.6 out of 5 average rating, 10 reviews

B15 Renovated Gem: 2bd/2ba +Pool w/Views, Walk2Ski

Condo in Lead

4.75 out of 5 average rating, 4 reviews

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

Condo in Lead

4.67 out of 5 average rating, 3 reviews

A4-Bright 2bd/2ba main floor corner unit

Condo in Lead

5 out of 5 average rating, 50 reviews

*New* Across from Terry Peak*Hot tub*Spacious

Destinations to explore