Holiday rentals with a pool in Elizabethtown

Spacious carriage house, heated pool all year!

This carriage house (1,150 sq.ft) is located on one of the most beautiful properties in the most beautiful small town in America. Located just minutes from downtown in the heart of Bourbon Country. Enjoy the year around pool and playground on the property! YES, SWIM ALL YEAR UNDER DOME. 2 adults + kids. Tree lined location close to restaurants, bars, shopping. apartment has a gorgeous interior, full kitchen, brand new pillow top bedding, new comfortable sofa bed. HD TV and internet on site.

Historic Estate Pool/Hot Tub, Louisville Retreat

Explore the renowned KY Bourbon Trail or the excitement of the Louisville KY Derby, only 45 minutes away. An ideal retreat for adventure & relaxation. Nestled on 2.1 picturesque acres near the Ohio River, this elegant historical home harmonizes classic charm & modern luxury. Prime location, adjacent to the River Walk boat launch, offers convenient access to water activities. Outdoor enthusiast will appreciate nearby hiking & biking trails at Buttermilk Falls & Otter Creek. Private Pool/Hot Tub.

LogCabin-15 min Bardstown Pool

• White Dog Lodge by Stylish Stay, a luxury home base on the Bourbon Trail • 15 minutes to Bardstown, 45 minutes to Louisville and Lexington • Designed for groups with multiple spaces to gather and unwind • Bourbon and cigar room for tastings and relaxed evenings • Massive game room and sports bar for shared downtime • Fully stocked kitchen for cooking and hosting meals together • Private hot tub year-round and seasonal pool for outdoor enjoyment • 6 bedrooms and 4 bathrooms for comfortable grou

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!

Koastal in Kentucky

Perfectly located just 8 minutes from The Elizabethtown Sports Park, home of the Cal Ripken Experience and Bluegrass Sportsplex of Elizabethtown, you will find this spacious and thoughtfully decorated, Coastal- inspired retreat, complete with a private pool, a theatre room and a large game room! To insure maximum comfort during your stay, each bed includes a pillow top mattress and all the extras such as coffee, detergents and swim towels are provided so you can simply enjoy your stay with us!

Close to Bourbon Trl/I65/KY Expo/Parks!

Large home with room to spread out! This home sleeps 11 with 5 queen bedrooms and one twin XL! You will find peace and quiet here with everything you need! Private swimming pool, FREE firewood, well equipped kitchen, large patio, large wrap around porch, vaulted ceilings, ceiling fans, and a charcoal grill. Extra large firepit with camping chairs for those fireside gatherings! This home is very convenient to Downtown Louisville, Churchill Downs, Bernheim Forest and all the Bourbon Trails!

Bourbon trail Oasis, Holiday Home. Inground pool

Countryside ranch home. Located along the Bourbon Trail. Also, near Mammoth Cave & Churchill D. 3 spacious bedrooms, 2 K, 1 Q bed. 3 Queen air mattresses also available. Quality linens. Modernized, open concept, Kit/dining seats 9 -15 people. New 2024 in is large screened porch, pergola & pool house, W/full bath & K/ wet bar. Wooded trails alongside water’s edge. Fire pits for s’mores & nature galore. Our nieces & nephews call it “Camp Uncle Kenneth”, our guests call it home away from home

Family reunion ideal. Trails/toys/goats/pool 7BR

Huge space inside&out! Secluded 50 acre wooded property of scenic trails/seasonal waterfall/creeks & star gazing platform plus 5200sf 7BRcountry home & pool. Great for family reunions w/multiple game/living areas; wood burning fireplace; 2 fully stocked kitchens; games/toys/books for all ages; cute goats to feed!; firepit area; heated pool (May-Oct); grill; decks. Near to Mammoth Cave, Lincoln Trail, Bourbon Trail, KY Derby! Disability/senior friendly w/stair lift. Come away-rejuvenate here!

The Bourbon Trail Getaway

Welcome to your cozy home on wheels! Nestled in a peaceful spot near downtown Elizabethtown, this stocked fifth-wheel camper has a comfy bed, kitchen, bathroom, A/C and Wi-Fi. Enjoy mornings with coffee, nights by the fire pit, or streaming your favorite shows. With outdoor seating, a grill, and all the essentials. You will also have access to the campground amenities to include the pool and a catch and release pond. It’s the perfect spot to relax, explore, or unplug in comfort and style.

Happy Goose Hollow

Come stay at this peaceful farmhouse right in the heart of bourbon country where you can enjoy the beauty of the country at a convenient location. We’re a quick drive to the start of the Bourbon trail (5mi from Jim Beam Distillery) and the beautiful Bernheim Forest. We’re less than 30 mins from the Louisville airport or Elizabethtown. Enjoy your evening by the fire pit around back or simply in the peace and quiet. Sunrises from a rocking chair on the front porch are sure to be enjoyed.

Sunsets on Bourbon Street! Waterfront views!

This lakefront home in Shepherdsville, KY, combines comfort and charm with New Orleans-inspired décor and bourbon accents. Featuring 4 bedrooms, 3 baths, a fully stocked kitchen, and spacious living areas, it’s perfect for families or groups. Outdoors, enjoy a covered deck, grills, and a dock with a bar, hammock, and fishing poles. Neighborhood amenities include a pool, playground, and clubhouse. Relax, fish, or savor sunsets—this home offers the ultimate getaway experience!

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.