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, 45 mins 2 Louisville

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!

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!

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.

Bourbon Trl Luxury Lodge*Pool*SpkEz*HotTub*GameRm

Luxury Bourbon Trail retreat conveniently located just 3 miles from Bardstown! Nestled on 11 lush green private acres away from neighbors, this 7,700 sq. ft. lodge features 6 bedrooms, 4.5 baths, a speakeasy lounge & bar, game room, massive hot tub, seasonal pool deck w/ pergola, fire pit, and chef’s kitchen. Plenty of room to spread out with multiple living room spaces and a dining room that seats 16. Perfect for family get togethers, work retreats, or Bourbon Trail getaways.

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.

Bourbon Retreat • Hot Tub + Game

* Hot Tub + Firepit • End your day under Kentucky stars with bourbon & laughter * Speakeasy Game Room • Arcade, poker, pool & bar TVs for friendly competition * 5 Bedrooms • Space to unwind, swap stories & wake to peaceful farm views * 10 Min to Distilleries • Willett, Heaven Hill & Lux Row adventures nearby * Fully Stocked Kitchen • Cook, sip & connect over bourbon-inspired meals * Seasonal Pool • Opens spring–summer with serene country views & privacy

NEW Nolin Lake+Hot Tub+Game Room+Pool+Pickleball

Brand new luxury retreat in the Paradise Grove golf cart community near Nolin Lake. This beautifully decorated home features 5 king bedrooms, a custom bunk room with four double beds, 3 en-suite baths, hot tub, fire pit, game room with ping pong and shuffleboard, and a spacious deck with outdoor TV. Enjoy access to pickleball courts, clubhouse, and community amenities, with a pool coming soon. Perfect for large groups and family lake getaways.