Holiday rentals with a pool in Pennington County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Pennington County rentals with a pool

House rentals with a pool

Guest favourite

Home in Lead

5 out of 5 average rating, 30 reviews

Crescent Moon Retreat

DawnRating, 5 stars1 month ago
Beautiful home cleaned to perfection. Beds were very comfortable. Hot tub was such a great addition. The house was so well stocked, everything you could need was there. Everything was just as described. The only issue we ran into was there were 12 of us, high school to 50s, & we had to take very quick showers throughout the day to have enough hot water. The host was so responsive & helpful & had someone out to make sure the hot water heater was functioning properly immediately. Would definitely stay in this lovely home again!!
Guest favourite

Home in Lead

4.91 out of 5 average rating, 32 reviews

Blackwoods Retreat in Powder House Pass w/Hot tub

HannahRating, 5 stars4 days ago
Great stay for our family vacation! Clean and very welcoming home. Perfect location. Would stay again!
Guest favourite

Home in Lead

4.93 out of 5 average rating, 30 reviews

Timber Trails: Pet-Friendly Haven for Adventurers

MandiRating, 5 stars4 weeks ago
Rung in the New Year with friends. Four adults, three kids, two toddlers, one baby and a dog made for a full but comfortable house. Our crew had so much fun playing ping pong and soaking in the hot tub. My only suggestions for improvement would be to provide a few more staples in the pantry (ex. Cinnamon, Garlic powder, paper plates, more paper towels).
Guest favourite

Home in Custer

5 out of 5 average rating, 14 reviews

Dwntwn Custer Farmhouse on Main St. with Hot Tub

JamesRating, 5 stars5 months ago
We really enjoyed or stay at Sarah's Airbnb. Everything you need is within walking distance, which was quite enjoyable. Although, it is on the edge of downtown, we had no issue with road noise, which was nice relative to the location. There is a grocery store across the street, so it was easy to walk over and buy food to prepare in the well equipped kitchen. The Pizza Mill restaurant was also across the street and there pizzas were outstanding. I would highly recommend this impendent and locally owned business. We also walked a block to breakfast one morning and ate at the Our Place restaurant. This locally owned breakfast diner was also a gem and had a wonderful hometown atmosphere. Further down the main street were several other shops and places to eat. The only negative issue with Sarah's pace was the narrow, steep, and winding stairwell to the second floor. None of our group over 50 felt comfortable staying upstairs. All and all a good stay.
Superhost

Home in Lead

4.9 out of 5 average rating, 30 reviews

Kickback Shack, Powderhouse Pass, Black Hills, SD

JamieRating, 5 stars1 month ago
Beautiful home in a beautiful development. Everything was exactly as pictured and our family had a wonderful Christmas staying here over the Holiday! Highly recommend!
Guest favourite

Home in Box Elder

4.94 out of 5 average rating, 33 reviews

Summer Swimming Retreat

RobinRating, 5 stars7 months ago
We had a wonderful stay and a memorable week! The house was very clean and had everything we needed. The front porch and back deck, patio, and pool where fantastic for relaxing after a busy day of hiking and site seeing. The set up of the house is great for multiple families (the cushy sectional on the garage level was my favorite!). The house is a short drive to restaurants and downtown Rapid City. We were able to Door Dash on nights when we didn't feel like cooking or going out. We were not successful in getting Uber or Lyft the one time we tried. The house is near the base so there is the very occasional rumble of a large plane nearby, but otherwise the neighborhood is nice and quiet. We didn't need to contact the owner for much, but when we did Jennifer was very responsive. I highly recommend!

Home in Keystone

4.8 out of 5 average rating, 84 reviews

Chalet Mt Rushmore VIEWS Hot Tub

MirandaRating, 5 stars3 months ago
We had a great time in the Keystone area and were happy to have this cute AirBnB to come back to after a long day of exploring…and the hot tub was a hit with the kids. My only suggestion would be to add 1-2 more lamps in the sitting/tv area.
Superhost

Home in Custer

4.81 out of 5 average rating, 26 reviews

Wind Dance Lodge w/ HOT TUB Large Shop garage

EmilyRating, 5 stars1 week ago
An amazing spot- Met up with a total of 8 people and had plenty of space to spread out. The kitchen was great for making food for us all and the table was fun to play games. LOVED the hot tub and game room. Right off a main road but still felt private and secluded.

Condo rentals with a pool

Guest favourite

Condo in Lead

4.9 out of 5 average rating, 59 reviews

Roomy Condo on the Mountain

JennyRating, 5 stars1 month ago
This was a great affordable place for a quick trip to ski for a few days. It worked great for our family of four. We were only a couple minutes from the slopes and simple short drive to the area for dinner options, etc.

Condo in Lead

5 out of 5 average rating, 3 reviews

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

BrandyRating, 5 stars19 months ago
beautiful location and lodg. it was perfect for our family to stay 2 bedrooms and baths. we spent the days at different attractions and then came home to a nice little space. no a/c, but it was always cool in the evening, so it was perfect. hot tubs were a great way to end the day. we stayed over the week of the 4th. it was just perfect.

Condo in Lead

4.75 out of 5 average rating, 4 reviews

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

BeatriceRating, 5 stars12 months ago
short walk to the ski lift and got to relax in the pool, hot tub and sauna! would highly recommend and hope to stay again soon!

Condo in Lead

4.67 out of 5 average rating, 3 reviews

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

JessicaRating, 5 stars25 months ago
We liked it even more than the photos. It was so nice to have two bathrooms. Living on the ground floor was easy for carrying our gear. We loved the hot tub! (Sadly our first night it was cold, so check before arrival if they will heat it). Nice to have access to pool table and extremely nice to walk to Terry Peak just across the street! (Tip buy lift tickets in advance for New Year’s Eve! Pick up passes night before so you can get right in gear rental lines). Hosts were very responsive. Nice to cook our own food.
Guest favourite

Condo in Lead

5 out of 5 average rating, 58 reviews

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

JoslynnRating, 5 stars1 week ago
We had a great stay! It had freshly snowed which made for beautiful scenery. The place looked exactly like the photos and we would definitely stay here again😊

Condo in Lead

4.88 out of 5 average rating, 8 reviews

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

JeffreyRating, 5 stars3 weeks ago
The rooms are perfect for short stay where you came to ski. The pool and hot tubs are great to loosen up in after a day on the slopes

Condo in Lead

5 out of 5 average rating, 4 reviews

B12 Original woodsy 2bd/2ba, walk to ski, hot tubs

MichaelaRating, 5 stars13 months ago
We highly recommend staying here if you’re planning to go skiing or snowboarding at Terry Peak. It makes the getting to and from the resort so easy and for us, lucky because they didn’t have large lockers for our boards so we had to take them home for the night. If we’d have stayed somewhere else that would have been a problem because we don’t have racks. Anyway, the unit was cozy and well stocked. The pool, hot tubs and game room are a nice option for unwinding too.

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