Holiday rentals with a pool in Elizabethtown

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.

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!

Best Location Elizabethtown, KY

Welcome to luxury living! Our spacious layouts, modern kitchens with high end appliances, and serene bedrooms and bathrooms. Guest enjoy access to exceptional amenities like high speed wifi, valet trash, our state of the art gym, outdoor grills, and seasonal pool. Whether you're working out, relaxing by the pool, or entertaining in the community spaces and ample free parking! You'll have the entire apartment unit to yourself which is 2 full bathroom, 3 bedrooms with a sleeper pull out couch.

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!

Pickleball*Hot Tub*Pool*Bourbon Trail*Sleeps 16!

Welcome to the Cabin at Rams Run! This newly renovated 5-bed, 5 full-bath cozy cabin is the perfect resort for adult trips and families alike. Situated on top of a ridge just above the James B. Beam Distillery, the cabin is in a perfect location directly between the culture and attractions of Louisville, and the distilleries of Bardstown--the bourbon capital of the world! After touring the Kentucky countryside, enjoy the hot tub, game room with pool table, or the indoor pickleball court!

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.

Retreat: Golf Sim, Massage Chairs, Summer Pool

Southern Luxe by Destino Getaways! ⛳ Golf simulator 🍿🎥 private cinema annex ♨️ Infrared sauna 💺 2 massage chairs 🧖wellness suite 📍 Minutes to distilleries 🌾 🛋️ Indoor and outdoor lounges 📖 🍂 🔥 Fire pit gathering area 🍽️ in/outdoor dining for 10 🌿 💦 Year-round hot tub 🏊 Seasonal pool (weather permitting) 🎱 Indoor billiards ♠️ ♦️ poker 🎲board games 🧩 puzzles 📶 Wi-Fi ✅ self check-in Designed for celebrations, bourbon trailblazing, retreats & unforgettable stays!

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.

4 BED/3 BATH on 20 acre Farm on KY’s Bourbon Trail

Escape the hustle and bustle of life and come enjoy a truly unique experience on this 20 acre farm! Perfectly located on KY’s Famous Bourbon Trail just off I-65 just outside of Louisville and Bardstown. This property has direct river access and features 4 bedrooms and 3 FULL bathrooms!! Split floor plan with TWO master suites. Large, spacious dining and living room. On the farm you’ll find neighboring horses, farm cats, hiking paths and plenty of places to explore!