Holiday rentals with a hot tub in Shelby County

An outdoor fire pit area is featured, surrounded by several adirondack chairs arranged on a gravel surface. String lights illuminate the space, creating a warm ambiance. In the background, the house is partially visible, with an inviting seating area under a canopy.

4.98 out of 5 average rating, 64 reviews

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Gather your crew for an unforgettable stay in Kentucky bourbon country. Magnolia Bourbon Manor is a beautifully restored historic home that sleeps 10, featuring a private speakeasy, covered hot tub, fire pit, and pool-table game room. Just 3 minutes from downtown Shelbyville, 12 minutes from Jeptha Creed and Bulleit, and 35 minutes from Louisville, it’s the perfect home base for Bourbon Trail adventures, weekends with friends, family getaways, and celebrations. Proudly hosted by a Superhost and

4.96 out of 5 average rating, 92 reviews

The covered porch is adorned with sheer white curtains and warm string lighting, creating a cozy atmosphere. Plush seating and a decorative rug invite relaxation. A hot tub and additional seating are visible, enhancing the outdoor living space's comfort and charm.

Cottage in Shelbyville

Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby

Soak in your private hot tub, step into a one-of-a-kind art gallery, and wake up 30 minutes from the Kentucky Derby. This renovated Victorian cottage blends spa-level comfort with local artistry, the perfect base for Bourbon Trail adventures, horse show weekends, or a group getaway nobody will forget. Three ensuite bedrooms, a gourmet kitchen, and a covered porch await. ✔ Hot Tub · Art Gallery ✔ 3BR/3BA Ensuite · Bourbon Trail ✔ KY Derby 30 min · BBQ Porch ✔ Wi-Fi · Smart TVs · Self Check-In

4.94 out of 5 average rating, 112 reviews

A circular fire pit area is surrounded by six blue Adirondack chairs, positioned on a green lawn. The cabin, featuring a green metal roof and wooden exterior, is visible in the background among tall trees and open space.

Cabin in Shelbyville

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

4.91 out of 5 average rating, 79 reviews

A hot tub filled with water sits invitingly, surrounded by greenery and a clear sky. A glass of whiskey rests on the edge, complementing the tranquil setting. The bubbles within the hot tub suggest relaxation awaits in this outdoor space.

Home in Simpsonville

*Distilleries close by* Hot tub*Firepit

Welcome to this beautiful, new 4 bedroom, 3.5 bathroom home ready to be the place for your bourbon trail stay! Centrally located just outside of Louisville. This home is less than 30 minutes from downtown Louisville where you can enjoy multiple distilleries, the Louisville Slugger Museum & Factory, Churchill Downs, the Fair & Expo, and just a short drive to Four Roses, Lexington and so much more! Air Hockey, hot tub, Golden Tee and fire pit are all waiting for your group to enjoy!

4.83 out of 5 average rating, 36 reviews

Home in Bagdad

*NEW* hot tub-sauna-large pool-game room-speakeasy

Escape to comfort and style at Expression on the Rocks: A newly renovated 6BR, 4400 sq ft retreat in the heart of the Bourbon Trail. Set on 5 lush acres with scenic views of hills and wildlife, this home offers a hot tub, sauna, inground pool, firepit, speakeasy w/poker lounge, and gameroom. Perfect for group getaways-just minutes from Kentucky’s world-famous distilleries. Who needs to be the center of the universe when you can stay in the center of the Bourbon Trail? Book Now!

5.0 out of 5 average rating, 23 reviews

HeatedPool~Sauna~ 2 HotTubs ~16 beds ~ Sleeps 25

🏠 𝐄𝐌𝐈𝐍𝐄𝐍𝐂𝐄 𝐃𝐎𝐖𝐍𝐒 🏠—KY luxury reimagined for big groups! Step into our recognized estate, explore our unrivaled amenities, and get ready to book your ultimate Bluegrass getaway. 🥃 HIGHLIGHTS: 🏊 Heated Pool & 2 Hot Tubs 🚿 outdoor shower 🧖 Barrel sauna 🔥Fire pit 🛏️ no bunks 🍿Cinema 🎤Karaoke 🎮Poker , Arcade & PS5 lounge 💅 Glam Suite 🧺3 dishwashers, dual laundry, and Starlink The ultimate home base for Bourbon Trail tours, reunions & retreats.

4.93 out of 5 average rating, 74 reviews

Peaceful Bourbon trail home POOL hot tub 3 kings

This quiet Bourbon Trail home is designed for groups, with three king beds, one queen, and a twin daybed. The hot tub, pool table, and fully-stocked kitchen make group meals and relaxation easy. Open living and dining areas provide space to gather. Outside, a large dining area and separate seating area let you unwind. Grocery stores, restaurants, and distilleries are all nearby. The pool is open May - September, and the property is maintained for comfort and reliability.

5.0 out of 5 average rating, 32 reviews

Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK

Jeptha Crest is a designer-built and thoughtfully decorated home, perfectly placed in the heart of the Bourbon Trail yet hidden among trees and nature views. Though centrally located, it feels like a private forest escape, offering rare privacy and calm. A spacious two-level deck, fire pit, hot tub, and sauna invite you outdoors, while inside, clean modern design blends seamlessly with warm, cozy comfort — a refined retreat created for slowing down and truly unwinding.

An aerial view showcases a spacious estate with bright outdoor lighting highlighting the landscaped grounds. A recreational area featuring basketball courts and seating is visible, offering ample space for outdoor activities, while the elegant façade of the home provides an inviting presence.

4.99 out of 5 average rating, 68 reviews

Kentucky Estate: Speakeasy, Theater & Sleeps 20

Oak & Ember Estate is an 8-bedroom Kentucky retreat sleeping up to 20 on 5 private acres. Hidden speakeasy with poker table, private cinema, converted garage game room with putting green and billiards, hot tub, pickleball court, and a gourmet kitchen built for groups. 30 minutes from Churchill Downs. The perfect home base for bourbon trail adventures, Derby weekend, family reunions, and corporate retreats. Guests say they never wanted to leave.

4.98 out of 5 average rating, 162 reviews

Home in Bagdad

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!

5.0 out of 5 average rating, 162 reviews

A log cabin is set against a vibrant sunset, highlighting its wooden exterior and spacious porch. Lush green grass surrounds the cabin, complemented by flower beds and gravel pathways. The rear showcases windows and entrance doors that invite natural light into the home.

Cabin in Frankfort

Sip on bourbon in the hot tub! +hiking & game shed

A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plentiful amenities on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!