Holiday rentals with a pool in Southern Indiana

Unique Luxury Family Retreat

This spacious 6 bedroom, 5 bath home is a perfect place for a family retreat. 25 minutes from CREATION MUSEUM, and 40 minutes from ARK ENCOUNTER, 20 minutes to Perfect North Slopes, this location is peaceful, quiet, and perfect for family vacations. 20x40 inground pool in the fenced backyard. Pet Friendly, Small Dogs Only. Large main floor living room, large basement entertainment area with 80 inch TV. Large bedrooms make this the perfect family getaway in the Cincinnati / Northern KY area.

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!

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).

Cozy Neighborhood Home - 10 min to Louisville!

Relax just 10 minutes from downtown Louisville at this beautiful patio home in a newly built community. Perfect for a weekend trip, business travelers, those with pets, travel nurses, and others! Quick, easy access to River City via I-65 or East End Bridge from a quiet, charming neighborhood just blocks from the area’s newest restaurant corridor. We are dog friendly, and boast a large side-yard and sidewalks throughout. Also enjoy the neighborhood’s paved walking trail with a lake view.

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

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.

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.

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.

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.

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.

Lake Cabin in the Woods

🌲Escape to peace and nature at Lake Cabin in the Woods! Unwind in your private hot tub, enjoy the shared pool, and soak up year-round tranquility surrounded by trees and wildlife. Located between I-70 and I-64, about 60 miles from Effingham, IL and Evansville, IN, our cozy cabin offers the perfect blend of seclusion and convenience—ideal for relaxing, recharging, and reconnecting with nature.

5BR Pool Retreat — Little 500 Weekend Available

Luxury 5BR retreat with indoor heated pool, theatre, game room, hot tub, and sauna. Perfect for IU games, family trips, and group getaways. Enjoy spacious living areas, a fully stocked kitchen, and room for everyone to relax. Minutes from IU, Memorial Stadium, and downtown. A rare Bloomington stay built for fun and comfort. Nightly price includes 15.5 % fee that airbnb charges it's hosts