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103 Houses

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City Gone Country Cabin

McKee house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

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Price per night from

$98

Brand New 2 Bedroom Townhouse

Middletown townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$2,182

Quaint and relaxing private room by the waterfront

Saint Matthews private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

Stylish Newly Renovated...just listed!

Columbia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$189

Charming Kentucky Derby rental

Louisville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,575

Beautiful home near Cherokee and Seneca parks

Louisville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$916

The Huston House

Bardstown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 42 minutes

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Price per night from

$258

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Price per night from

$401

Highlands Derby Rental

Louisville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,718

Hill n Dale Thoroughbred Horse Farm at Xalapa

North Middletown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,374

⁕Whiskey Business* Bardstown Bound*Heaven Hill*

Springfield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$205

Cool 1908 Bungalow on Woodland Ave Downtown Lexington KY! BY UK

Lexington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 11

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Price per night from

$144

Exquisite Spa Theme Luxury Stay near Waterfront

Saint Matthews private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

Charming 4 bedroom home minutes from Downtown!

Jeffersonville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$184

Bluegrass Serenity

Georgetown house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,374

Home away from home ❤️

Lexington house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

Wonderfully Quaint Cottage Near Downtown, UK and RUPP

Lexington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$137

Quirky Midcentury Lake Cumberland Bungalow

Burnside house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$172

Wooded Retreat PLUS Derby

Louisville house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,718

Cabin on the lake

Nancy cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$252

The Orange Door - Derby Perfect Sleeps 10

Louisville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$286

Private Room

Lexington house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$52

GERMANTOWN GEM CLOSE TO EVERYTHING DERBY!

Louisville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$2,290

little 'peace' of paradise - near Louisville

Taylorsville cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$148

Quiet and Peaceful - A Cabin in the Woods

London log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$172

Large Historic Home, Walk to Dinner, parks, cafes!

Louisville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 3 hours 6 minutes

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Price per night from

$516

Little Cabin In The Woods Peaceful Retreat

East Bernstadt log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 10

“Best hospitality in Kentucky!” We absolutely loved our stay in this cabin in the woods! Had all of the amenities needed and lots of extras! We will definitely be back!!

Responds fast! avg. 14 minutes

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Price per night from

$102

Four Seasons Lake Cottage in Kentucky on the Bourbon Trail

Taylorsville cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$212

Countryside (Vacation) Getaway

Hodgenville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 25 minutes

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Price per night from

$178

Quiet & safe 2 bed 1 bath in Crescent Hill

Louisville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$149

6 Bedroom Italianate Mansion in Historic Zone, Wall to All!

Louisville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

“Great House!” We stayed for Ford Iron Man for 5 nights. 7 adults, 2 teens, 1 child. Stunning home- not your average rental house, but a huge, stately place that still has everything from plasma TVs to wifi. We arrived a little early to find the homeowner and housekeeper still prepping house. A little awkward, but the rest of the stay was perfect. Also, ALL 3 of us FINISHED THE RACE!!! My husband's two teenage girls loved the neighborhood and my sister's little boy played in the nearby park.

Responds fast! avg. 3 hours 6 minutes

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Price per night from

$1,140

LOUISVILLE - PGA, DERBY, BOURBON Done right! Centrally located

Saint Matthews house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,718

Home rental

Louisville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$567

Pool, Tennis Court & Billiards! Oak Hill Property

Ferguson house

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 31

Responds fast! avg. 4 minutes

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Price per night from

$1,145

Bluegrass Boujee

Lexington house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

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Price per night from

$915

The Bunkhouse

Kings Mountain house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$258

Angels Envy 29 - A relaxing place by the lake!

Taylorsville apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$171

Hygge Creek Cottage BB& Private Guest Boutique

Taylorsville house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$229

Viewing 38 of 103
rentals in Harlan

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