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Lexington Holiday Rentals

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    Travellers to Lexington are booking October dates now. Secure your holiday rental today, and have the perfect trip.
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    Charming Row House Near Downtown1 / 37
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Classic Cape Cod Near Downtown, UK, Hospitals1 / 59
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Downtown Lexington Guest House1 / 22
    (7)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway1 / 13
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky 40505
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Excellent Location! Close To Shopping, Restaurants And More!!1 / 8
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky 40515
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Guest House on Kentucky Working Thoroughbred Horse Farm1 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky 40505
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Four Bedroom Cape Cod Sleeps up to 81 / 24
    (14)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky 40504
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Br 1 Ba Close To Equestrian Events And University Of Kentucky Athletics1 / 8
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky 40505
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Cottage * Castlewood Park1 / 21
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Lexington, Kentucky 40505
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Breath of Fresh Air... Jordan Hill Farm1 / 26
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    • Mountain Views
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    Reviewed 4 May 2014
    Everything was wonderful. The home was very comfortable and lovely and clean. A very friendly and homey environment. Cant wait to stay again.
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    About this property
    Get back to Nature. Close to Lexington, Relax & Revitalize, Fun for Golfers to come and relax, Family reunions, retreats and more.... 3 Bedroom 3 Bathrooms, Country Home Nestled In The Heart Of The Bluegrass Make our home. . . your home. Located 30 minutes from Lexington, KY. Stay on the 85 acre...
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    Lexington, Kentucky 40475
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5BR, 3BA Close To Equestrian Events And University Of Kentucky Athletics1 / 18
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Lexington, Kentucky 40505
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    This one bedroom condo is the perfect place to stay in downtown Lexington. You will be close to Rupp Arena, the Square, Cheapside Park, the Hilton Hotel, Lexington Convention Center, numerous restaurants and night spots. Condo is newly purchased and has just undergone a total renovation (new...
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    Lexington, Kentucky 40507
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Location Information
    Lexington, Kentucky 40505
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stylish Condo in Flourishing Downtown Lexington1 / 18
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
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    Reviewed 6 September 2015
    This place has it all! Communication with the owners before the trip was great, all of my questions were answered within minutes. Check-in was a breeze thanks to very detailed...
    Reviewed 1 July 2015
    Our book club stayed here for a long weekend and it couldn't have been more perfect. We had 5 ladies that fit nicely. One took the couch but we had the option to get a air...
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    About this property
    Stay in a one-of-a-kind property half-a-block from the Hyatt and Rupp Arena and one block from the Hilton in the heart of downtown Lexington. Every room makes a statement with vibrant artwork, bold architecture and real hardwood, granite & marble flooring throughout. There are 2 bedrooms, one with...
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    Lexington, Kentucky 40508
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Mulberry Hill on West Fourth is a newly constructed townhouse in the heart of Lexington's historic district. Gleaming wood floors paired with clean modern design offer the ultimate city living vibe. Cozy, artsy, clean - the perfect place to hang your hat for a visit to Lexington! Inside, a spacious...
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    Lexington, Kentucky 40508
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Case Verde is a 1937 bungalow lovingly updated and nestled on the historic street of Transylvania Park just steps from UK's campus. It is a 3 bedroom, 2 bath home with a beautifully restored large loft that sleeps 4 to comfortably sleep a total of 10 guests. An artist's dream, there is beautiful...
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    Location Information
    Lexington, Kentucky 40508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    15 Min to Keeneland/KY Horse Park/Red MileRacetrack/Airport/Downtown Lexington1 / 33
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2017
    You can not go wrong renting this property. It was amazing! Me & my family had all the amenities of home. Very clean,neat and spacious. It's close to town for your great...
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    About this property
    Quiet & Convenient 3 BR/2 BA.Just 15 minutes to Keeneland race track, Lexington Airport & Downtown Lexington, the Kentucky Horse Park and the Red Mile Race Track as well as Fayette Mall & Lexington Green. Convenient access to a plethora of restaurants & a 24 hour Kroger supermarket w/ a Starbucks...
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    Location Information
    Lexington, Kentucky 40511
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Centrally located to EVERYWHERE, you want to be in Lexington. Less than 2 miles from 3 new Breweries, Downtown/Rupp, Convention Center, UK Campus and Commonwealth Stadium. 5 miles to the Red Mile Racino. Less than 8 miles to Keeneland, and BG Airport. Fast access to Georgetown, KY (Toyota), New...
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    Lexington, Kentucky 40508
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Hart-Featherston House1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • DVD Player
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    • Outdoor Dining Area
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    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2014
    Stayed for nine days and had a really delightful time. Very comfortable beds, nicely furnished. Lovely little touches around the house to make my stay more pleasurable. Kitchen...
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    About this property
    The Hart-Featherston House is the second-oldest home in Lexington and is RICH with history! It has been completely restored and provides character that is not found ANYWHERE! Combining modern luxuries with the comforts that only historical homes can provide, the house sits on 1.24 acres and has...
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    Location Information
    Lexington, Kentucky 40515
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Central Heating
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    Pet friendly
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    About this property
    Historic Morrison Cabin is the oldest home in Lexington on its original foundation. It was built by John Morrison in 1787 when Kentucky was still a part of Virginia. John Morrison was one of Lexington's founders. He built the home for his wife, the first woman to live in Lexington. It is ideally...
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    Lexington, Kentucky 40508
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    15 minutes to Keeneland, the KY horse Park, the Red Mile, Downtown Lexington, the University of Kentucky & Translyvania University. Great location for touring the Bourbon Trail. Fully equipped kitchen w/ refrigerator w/ ice maker, stove, microwave, dishwasher, disposal, Keurig, toaster, crock pot,...
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    Location Information
    Lexington, Kentucky 40511
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky 40502
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Location Information
    Lexington, Kentucky 40502
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Excellent Location!1 / 9
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Reviewed 2 July 2017
    This was a great stay and area for our family of 4 and 2 small dogs. The home was very welcoming and clean and had a great back yard. The owners checked in with us to be sure...
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    About this property
    Home sleeps 5+ people. 3 bedroom 1 1/2 bathroom conveniently located in a central location with a short drive to all major attractions in Lexington. Home is equipped with a 4 burner stove, microwave, refrigerator, dishwasher and garbage disposal. Also a washer and dryer for your convenience to...
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    Lexington, Kentucky 40515
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A hidden gem in Lexington's Historic District1 / 13
    (42)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky 40508
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    KY Horse Park/Summer Vacation/Golf Trip/Keeneland! 4 mi off I-75/I-641 / 24
    (1)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 17 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Lexington, Kentucky 40509
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 17
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    Luxuriously Appointed Executive Home Minutes From Keeneland, Airport & Downtown1 / 24
    (28)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Lexington, Kentucky 40510
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    1.5 Miles to Kentucky Horse Park1 / 13
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky 40511
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Country Cottage on a horse farm, near Keeneland and the horse park1 / 18
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Lexington, Kentucky 40510
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    All The Comforts of Home1 / 24
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky 40511
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bdr/3 Bath House in Andover Convenient to All of Lexington1 / 21
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky 40509
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Morrison Cabin Offers The Finest Interiors, Unique History And Best Location1 / 24
    (16)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Lexington, Kentucky 40508
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Renovated Downtown Lexington Apartment1 / 11
    (34)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lexington, Kentucky 40508
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beautifully Restored 1880 Brick Home Downtown1 / 19
    (7)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky 40502
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!1 / 24
    (36)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Lexington, Kentucky 40511
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Nice Cozy Apartment In The Heart Of Lexington, Kentucky1 / 24
    (17)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky 40515
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Downtown Townhome Near Rupp Arena1 / 13
    (21)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky 40508
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury Accomodations- Perfect for Keeneland, Horse Park, Rupp Events, and more!1 / 24
    (7)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Quiet oasis of handmade charm and natural beauty downtown Lexington1 / 24
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    Location Information
    Lexington, Kentucky 40502
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Historic Downtown Lexington Condo - Turn of the Century House1 / 17
    (9)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    Location Information
    Lexington, Kentucky 40508
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants1 / 24
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    3BR Penthouse In Historic Downtown W/Free WiFi, Walking Distance To Restaurants1 / 24
    (32)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Close To Everything!1 / 13
    (32)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Location Information
    Lexington, Kentucky 40507
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Best of Both Worlds! Country Living Just Minutes from Town!1 / 23
    (15)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Lexington, Kentucky 40509
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Completely refurbished downstairs apartment in 1920's home1 / 18
    (17)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beautiful Historic Home with Modern Amenities1 / 24
    (10)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Lexington, Kentucky 40515
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1.7 miles to KY Horse Park1 / 23
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lexington, Kentucky 40511
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy Downtown Townhouse1 / 17
    (5)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    A Renovated 3 Bedroom, 2.5 Bath Townhouse In Downtown Lexington.1 / 16
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Lexington, Kentucky 40508
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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