Vacation rentals with a pool in Southern Indiana

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

Value · Family · TV

Peaceful Paradise LOWER Fam 2BR Hot Tub/Pool/SAUNA

Located just 20 minutes from CVG airport, Perfect North Slopes, and the Creation Museum—come & enjoy a piece of Indiana in our 2 bedroom apartment! After a long day exploring our local parks or skiing on the slopes, soak in the hot tub or pool overlooking the valley or enjoy your evening by the fire pit! An in-home entertainment surround system will bring whatever movie you choose right into the room with you! Access to apartment is down stairs --not wheelchair accessible. Pool open 5/22-9/1

Family · Value · Condition

YOUnique 3+ bedroom, spa/hot tub, huge deck

Our place is close to Indiana University, IU athletics, I-69/37 to Indianapolis, great views, family-friendly activities, nightlife, restaurants and dining. You’ll love our place because of the privacy - and the friendly neighbors (us), the beautiful outdoor space, the kitchen/great room, the hardwood floors, and the volleyball court and large yard. Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets - but no cats).

Family · Value · Comfort

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

Family · Location · Laundry

Lake Front w/ Pool! Between Ark & Creation Museum.

If you are looking to experience lake life, look no further! Our Guest House sits on the beautiful 140 acre Bullock Pen Lake. It's a great place to relax, or enjoy kayaking, paddle boating, paddle boarding and fishing. We have one of the best views of the lake. The Guest House is fully renovated and decorated with relaxation in mind. It has everything you would need for your stay. After all, the lake is where your worries fade and memories are made! (The pool is now OPEN!!!) 5/11/26

Value · Family · Sleep quality

Hattie's Hill Cottage

Cozy cottage located just behind the main home on the property (see photos). Relax by the pool, open seasonally, which is shared by the main house guests and host family, or enjoy an evening stroll out in the country. Conveniently located near Owensboro, Rockport, Hawesville, and Lewisport. The cottage features one flexible bedroom with either two twins or one California king, TV, well-stocked kitchen, dining/work space, comfortable recliners, and access to the beautiful grounds.

Location · Family · Layout

The Getaway House with Hot Tub and Pool

Enjoy the beautiful hot tub year round with the woods as your view, along with a screened-in area on the back deck and a semi-inground, heated swimming pool! Roasting marshmallows over a campfire is perfect for those cool evenings on the large concrete fire pit (firewood is available, free of charge). Metal skewers and a charcoal grill provided (bring your own charcoal/lighter fluid). Pool open 6/6 -9/7/25. This charming 2 bdrm, 1 bath home is perfect for families or couples.

Family · Location · Air conditioning

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

Welcome KY visitors, horse lovers, Bourbon Trail guests, or anyone looking for a getaway! This is a somewhat rustic, homey, comfortable 20 year old cottage. It's not perfect, but our guests find it charming and sufficient. You'll find the home exactly as described with the offerings and expectations. Rest, relax, and recharge in a gated community overlooking Taylorsville Lake. Don’t be another hotel's customer when you can stay in a spacious home with a Jacuzzi J-235 hot tub.

Value · Family · Pool

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful trees. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Value · Family · Hiking

Entertainer's Dream w/ Pool and Games

You won't find a more well equipped home in the area than you will at Hometown Hideaway. Hometown Hideaway is luxury at its finest with 4 bedrooms, 2.5 baths, 2 separate living spaces, plus an amazing game room with pool table, 65" Smart TV, shuffleboard, and plenty of seating. Don't forget the fenced backyard with private heated pool and seating galore for you and all of your guests. Plenty of room for rest and relaxation indoors and out.

Value · Location · Backyard

Captain Bill’s Lake House Heated Salt Water Pool

Captain Bill’s Lake House. This majestic A-frame is at the entrance to the Cataract Lake boat ramp. The house will accommodate up to 7 guests, with three bedrooms and two full baths. All guests have full access to Captain Bill’s shared heated salt water pool and surrounding gardens. Boat parking is available on the property, inquire for details. Heated Salt Water Pool is seasonal beginning May 1, through September 30th.

Location · Family · Amenities

Little Slice of Heaven-27

Welcome to Cottage 27! Our "Little Slice of Heaven" overlooks Taylorsville Lake, just 25 minutes from Louisville. Cottage 27 is equipped with a full kitchen, outdoor grill, washer & dryer, smart TV's, dvd player & large selection of games. Cabin 27 is the perfect location to stay if visiting the lake, just getting away from it all or for those traveling the wine or bourbon tours in the area.

Location · Value · Pets