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Vacation Rentals nearby Rupp Arena

432 West Vine St., Lexington, Kentucky 40507
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    Travellers to Lexington are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 80 Rentals in Lexington
    Charming Row House near it all!1 / 15
    (3)Excellent
    1.6 kilometres from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    0.6 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Morrison Cabin Offers the Finest Interiors, Unique History and Best Location1 / 15
    (2)Excellent
    0.6 kilometres from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    1.5 kilometres from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 11 Quick View
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    About this property
    Property has 2 queen beds (each in their own room) with door, one bedroom off bathroom and kitchen, other is larger in front of house with large bay window overlooking a beautiful tree lined street of historical homes - we have a full size futon couch, twin size roller bed and several full size...
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 11
    6.9 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    MONTH-to-MONTH and LONG-TERM rates at hefty discounts available by request. Great for horse or Bourbon Trail touring, Keeneland Racing, the Rolex Three-Day Event, Kentucky Horse Park events, conventions and trade shows, UK Sports and Graduations, across from Lexington Tennis Center. Just 5-10...
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'The Guest House', Located on a 300 acre horse farm.1 / 26
    (2)Excellent
    12.5 kilometres from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    7.1 kilometres from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Brick Ranch Dwelling on Quiet Court The convenient setting is on a very quiet court which provides for additional privacy and security. The Brick Ranch has an eat in kitchen and private patio with gas grill which provides for a relaxing atmosphere. The property is located near great shopping and...
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    1900 Home Just Restored to Last Another Century1 / 32
    (4)Excellent
    1.9 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 10
    Town home with private garage and backyard1 / 18
    (7)Excellent
    2.0 kilometres from Rupp Arena
    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 3 Bathrooms, Sleeps 2
    Springwood Cottage in the Heart of the Bluegrass1 / 25
    (16)Excellent
    15.0 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6.3 kilometres from Rupp Arena
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Easy living awaits when you book this charming 5-bedroom, 3.5-bathroom vacation rental house in Lexington. With enough space for up to 9 guests, this home is the perfect destination for those wanting to rest and relax in a homey environment. When you’re not out exploring the abundant excitement of...
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    Lexington, Kentucky
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Downtown Lexington Condo - Turn of Century House1 / 8
    (1)Excellent
    0.5 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed May 28, 2014
    We were so pleasantly surprised by our rental! It is exactly as pictured. The owner was so easy to deal with. The condo is equipped with everything you can imagine, even a...
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    About this property
    Cozy condo fully redone in 2008. Turn of the century Victorian house, top floor, original hardwood, lead glass, vaulted ceilings, granite, jacuzzi, tile shower, fireplace, DVD/CD/wireless. Fully equipped gourmet kitchen, dining nook, furnished with fabulous antiques and contemporary furniture and...
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Historic Studio in Downtown Lexington. 1 block from Main Street and Rupp Arena/Convention Center on quiet and historic Mill Street. Walking distance to UK, restaurants, bars, breweries, distilleries, shopping, and everything else in downtown Lexington! You can not ask for a better location than...
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    6.3 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    About this property
    Cozy two story former model home situated on Lexington's North side offers quiet, safe space to relax and enjoy the scenic area. You are 10 minutes from downtown and University life as well as 1 hour outside of Louisville and Cincinnati. This property features a private room that includes 1.5 bath...
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    4.7 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Convenient 1st floor condo, Park 20' from door, Quite/clean neighborhood, No stairs, 2 steps, Easy access for limited mobility guests, Hand rails in main bathroom, 805 sq. feet, Sleeps 6 to 8 Large dining table for 6, Fully equipped kitchen, Refrigerator, Microwave, Dishwasher, Wall to wall carpet...
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    5.7 kilometres from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Welcome to Lexington! Stay in our cozy place and enjoy the southern charm. Lexington is also famous of its horses, bourbon, basketball, and beautiful bluegrass scenery. This house is a short distance away from many of the amenities, it is walk-able to many great restaurants and shopping, Arboretum...
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Bourbon Barrel Suite1 / 44
    (23)Very good
    0.6 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-641 / 40
    (21)Excellent
    11.2 kilometres from Rupp Arena
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Luxury Updated Chevy Chase Home - Close to UK1 / 16
    (61)Excellent
    2.4 kilometres from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms1 / 11
    (14)Excellent
    1.5 kilometres from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bdr/3 Bath House in Andover Convenient to All of Lexington1 / 37
    (169)Excellent
    8.6 kilometres from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    The Black Bear Lodge1 / 28
    (15)Very good
    0.6 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Cheerful and Cozy in the Heart of Chevy Chase!1 / 15
    (32)Excellent
    2.5 kilometres from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Kimball Suite-3 bedroom / 2 Bathroom1 / 49
    (27)Very good
    0.6 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway1 / 8
    (69)Excellent
    5.8 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Beautiful Woodward Heights Townhouse!1 / 25
    (12)Excellent
    0.9 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Kathy's Place Near downtown/Rupp, UK, Horse Park1 / 27
    (16)Excellent
    2.2 kilometres from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech1 / 15
    (21)Excellent
    0.4 kilometres from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Guest House on Kentucky Working Thoroughbred Horse Farm1 / 12
    (42)Excellent
    5.4 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    The Wine Cellar Condominium1 / 37
    (37)Excellent
    0.6 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Welcome to your new Hartland home!1 / 15
    (5)Very good
    9.5 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.7 miles to KY Horse Park1 / 18
    (56)Very good
    10.3 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Adorable 2 bedroom, 3 bathroom townhouse downtown with reclaimed boutique  decor1 / 25
    (45)Excellent
    1.7 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Awesome House for a Football Weekend or Keeneland1 / 24
    (1)Excellent
    3.3 kilometres from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    JW's LOFT Near downtown/Rupp Arena, UK, Horse Park1 / 36
    (13)Very good
    2.2 kilometres from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    Private Lake/Farm Retreat1 / 16
    (35)Excellent
    20.0 kilometres from Rupp Arena
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
    The Kentucky Bourbon Suite1 / 48
    (32)Excellent
    0.6 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Private Apartment in Downtown Lexington1 / 7
    (46)Excellent
    0.4 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    * Available for Lease as a Furnished Executive Rental * 35% Discounted Rate *1 / 18
    (9)Very good
    14.5 kilometres from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Bungalow Bill's near downtown Keeneland Horse Park1 / 50
    (12)Excellent
    2.8 kilometres from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Lexington Apt. with parking & private entrance Preview listing1 / 10
    (31)Excellent
    9.3 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Historic Downtown Private Room and Bath1 / 11
    (23)Excellent
    1.2 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.8 kilometres from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Sport your best blue and cheer on the Kentucky Wildcats from this vacation rental house! With 4 bedrooms, 2 bathrooms, multiple living areas, and a charming yard, this house invites you to make yourself at home. Located just 2 miles from the heart of Lexington, this property is perfect for anyone...
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    6.7 kilometres from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
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    • Balcony
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    • Terrace
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    Pet friendly
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    About this property
    Open and airy from the moment you walk in as an enclosed sunroom provides wide, screened windows that open to let in the fresh air. Comfortable furnishings including recliner and cozy reading/conversation chairs provide adequate seating for you and/or guests. Smart TV in living room. Wi-Fi...
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.0 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Whether you're in town for the horses, history, bourbon, or bluegrass, this vacation rental puts you close to it all! This charming 3-bedroom, 2-bathroom property is the perfect place to call home while you experience all that Lexington has to offer. Enjoy fun-filled days spent strolling downtown...
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    7.4 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get the best of country living and city sights when you stay at this Lexington house! Boasting a private location and wide-open spaces, this 3-bedroom, 2-bathroom vacation rental is perfect for families with a wide range of interests. Spend the day at the racetrack and betting on horses, or go...
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury 5BR/4BA Updated Home In The Heart Of Lexington1 / 40
    (26)Excellent
    5.5 kilometres from Rupp Arena
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    1.5 Miles to Kentucky Horse Park1 / 13
    (43)Very good
    10.5 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Thoroughbred Suite1 / 50
    (18)Very good
    0.6 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    6.2 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    About this property
    3 Bedroom Williamsburg House in the Heart of the Bluegrass Master Bedroom on first floor with a Tempur-Pedic King bed with seperate remotes, bathroom off the bedroom with shower and tub 2 large bedrooms upstairs with a full bath - 1 king and 1 queen with a full sleeper sofa Main floor has living...
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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