Properties

10 properties  

$3,281/night

Private Historic Manor | Derby Week Exclusive

OwnerRez
4 Bedrooms • 6 Baths (4 full, 2 half) • Sleeps 2-8
Internet
Offered exclusively for Kentucky Derby week, this distinguished estate is a once-a-year opportunity to stay in one of Louisville’s most prestigious and historic neighborhoods. Set within a storied enclave along River Road, the home blends Old-World craftsmanship with refined modern comforts—creating a setting that feels both timeless and indulgent.

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$4,500/night

Creekside Luxury Retreat on 22 Acres

OwnerRez
5 Bedrooms • 4 Baths • Sleeps 8-14
Internet Fireplace

Tucked away in the woods of Persimmon Ridge Golf Course, The Sycamore place offers breathtaking views overlooking 22 acres on Floyd's Fork Creek. Perfect for Bourbon Trail, Derby, and Louisville dining guests!

**This listing is hosted by the owners Annie B. and Eli B. with assistance from Bourbon Rentals. You may speak with Annie, Eli, Brandon, or Kayla before, during, and after your stay.**

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$15,000/night

Harris House - Rustic Farmhouse on 200 Acres

OwnerRez
5 Bedrooms • 5 Baths (4 full, 1 half) • Sleeps 2-12
Internet Firewood Provided Forest

✨ Complimentary S’mores Kit with Every Stay ✨

Staying here feels like stepping back into a simpler time. This home offers a quiet, peaceful farm experience where mornings are unhurried, evenings are calm, and the noise of everyday life fades away—yet you’re still conveniently located near all that Louisville has to offer. It’s the rare balance of true countryside serenity with easy access to the city.

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$319/night

"On the Rocks" Bourbon Trail Getaway

OwnerRez
5 Bedrooms • 3 Baths • Sleeps 2-14
Internet Fireplace Lake View Hot Tub

Sleeps 13 | 5 Bedrooms | 3 Bathrooms | Hot Tub | Pool | Trails | Wildlife

This spacious 5-bedroom, 3-bath lake cottage features a private hot tub, private jacuzzi tub, access to a sparkling community pool, hiking trails, and wildlife views—perfect for groups up to 13. Enjoy a fully equipped kitchen, arcade game, jetted tub, fireplaces, smart TVs, and balconies with partial lake views. Just 2 minutes from Taylorsville Lake Marina and 40 minutes from Louisville, it's the ultimate Bourbon Trail base camp.

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$159/night

3BR/1.5BA Home w/ Relaxing HOT TUB in Popular Area

OwnerRez
3 Bedrooms • 2 Baths (1 full, 1 half) • Sleeps 1-6
Internet Hot Tub
Make memories in 'The Gateway to the South' when you book this 3-bedroom, 1.5-bathroom house! Featuring over 1,500 square feet of living space, a full kitchen, and all the comforts of home, this vacation rental is perfect for families and groups of friends visiting Louisville. Catch a race at Churchill Downs, take a tour of the Louisville Slugger Museum, walk to popular local restaurants, or taste your way along the Bourbon Trail. Whatever you plan to do - this is the perfect home base.

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$109/night

Liberty Belle - 3BR/1.5BA Sleeps 6 Near NULU

OwnerRez
3 Bedrooms • 2 Baths (1 full, 1 half) • Sleeps 3-6
Internet Downtown

This historic brick home with lots of updates brings comfort and coziness to urban living.

Our downtown home is only a 2-minute walk from the vibrant commercial district of NuLu. Perfectly situated between Downtown Louisville, the historic Highlands neighborhood, and trendy Butchertown, you’re a minimum rideshare fare from anywhere and everywhere you’ll want to be.

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$79/night

Stylish Loft in Vibrant Neighborhood

OwnerRez
2 Bedrooms • 1 Bath • Sleeps 2-4
Internet
NEWLY RENOVATED 2 Bed 1 Bath loft is perfect for small groups, couples, or business travelers. Upon arrival you'll be greeted by the brand new modern kitchen and original 100 year old refinished hardwood floors. The quaint sitting area is perfect for taking a break from the days activities. Two private bedrooms with new comfortable bedding (1 king, 1 queen) and a brand new modern bathroom make this loft the perfect space for a trip to Louisville.

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$3,360/night

The Charred Oak Estate

OwnerRez
5 Bedrooms • 4 Baths • Sleeps 4-12
Internet Fireplace Private Pool

Welcome to your private Louisville retreat! This stunning 5-bedroom, 4-bathroom luxury home is the perfect escape for families, groups, or business travelers seeking space, comfort, and style. Nestled in a quiet neighborhood just minutes from downtown, this property is designed for both relaxation and entertaining.

💎 Highlights:

Spacious layout with 5 beautifully appointed bedrooms & 4 full bathrooms

Resort-style pool with lounge seating and peaceful landscaping

Custom outdoor kitchen featuring a built-in grill, fridge, dining area, and a wood-fired pizza oven

Fully equipped game room – ideal for movie nights, board games, or just hanging out

Private workout room with cardio and strength equipment

2-car garage + ample driveway parking

Chef’s kitchen, cozy living spaces, and high-end finishes throughout

Whether you're in town for the Bourbon Trail, Derby season, or a luxury weekend getaway, this home offers a perfect blend of comfort, style, and convenience in the heart of Louisville.

🛏 Sleeps up to 12 guests comfortably
📍 Centrally located with quick access to top attractions, dining, and entertainment

Your Louisville luxury stay awaits—book now!

Fine print:
-Pool open Memorial Day through Labor Day
-Pool and lawn maintenance are on site twice per week to keep the property and pool in great shape
-By confirming a reservation, guests consent and agree to allow maintenance workers on the property at any time to care for the pool and grounds

RENTAL AGREEMENT: Guests are required to sign all Rental Agreements prior to check in. If guests refuse to sign the rental agreement, the cancellation policy will still apply.

KENTUCKY DERBY: All Kentucky Derby week/weekend reservations are non refundable, regardless of whether or not a rental agreement has been signed.

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$8,500/night

The Estate at Hazelnut Farm

OwnerRez
4 Bedrooms • 5 Baths (4 full, 1 half) • Sleeps 2-10
Allows pets Internet Fireplace Private Pool

A Private, Gated Lakeside Retreat of Distinction

Welcome to The Estate at Hazelnut Farm, an elevated, design-forward retreat where refined luxury meets serene natural beauty. Privately gated for added seclusion, this extraordinary 4-bedroom, 5-bathroom residence is situated on the pristine grounds of the Hazelnut Farm Event Estate, offering an unparalleled stay for discerning guests seeking privacy, elegance, and unforgettable surroundings.

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$3,500/night

Storybook Stone Home | Groups On the Bourbon Trail

OwnerRez
5 Bedrooms • 3 Baths • Sleeps 2-13
Internet
Fully renovated in 2026, this 5BR/3BA stone cottage is your ideal Bourbon Trail home base in Lawrenceburg. Comfortably sleeping up to 13, it offers a perfect mix of space to gather and room to unwind, plus a large shaded backyard with a patio for relaxing mornings and evenings. Clean, well-stocked, and thoughtfully designed—just a smooth, easy stay from start to finish.

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