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Vacation Rentals near Rupp Arena

432 West Vine St., Lexington, Kentucky 40507
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    Travelers to Lexington are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 133 Rentals in Lexington
    Charming Row House near it all!1 / 15
    (3)Excellent
    1.0 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    0.3 miles 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
    0.3 miles from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    0.9 miles 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 11
    4.3 miles 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
    (4)Excellent
    7.8 miles from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    4.4 miles from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    1900 Home Just Restored to Last Another Century1 / 32
    (7)Excellent
    1.2 miles from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 10
    Town home with private garage and backyard1 / 30
    (14)Excellent
    1.2 miles from Rupp Arena
    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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    Lexington, Kentucky
    Rental Home - 1 Bedroom, 3 Bathrooms, Sleeps 2
    Springwood Cottage in the Heart of the Bluegrass1 / 25
    (24)Excellent
    9.3 miles from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Downtown Lexington Condo - Turn of Century House1 / 8
    (1)Excellent
    0.3 miles 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
    3.9 miles 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
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
    3.5 miles 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Bourbon Barrel Suite1 / 44
    (27)Very good
    0.3 miles from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 Bdr/3 Bath House in Andover Convenient to All of Lexington1 / 37
    (194)Excellent
    5.3 miles from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location1 / 24
    (85)Excellent
    0.3 miles from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Spacious updated 4 bedroom house near Kentucky horse park1 / 29
    (24)Excellent
    3.8 miles from Rupp Arena
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Cheerful and Cozy in the Heart of Chevy Chase!1 / 16
    (52)Excellent
    1.5 miles from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Woodward Heights Townhouse!1 / 25
    (18)Excellent
    0.5 miles from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech1 / 13
    (44)Excellent
    0.3 miles 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
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    Guest House on Kentucky Working Thoroughbred Horse Farm1 / 12
    (55)Excellent
    3.3 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lexington, Kentucky
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    The Wine Cellar Condominium1 / 38
    (55)Excellent
    0.3 miles from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Welcome to your new Hartland home!1 / 15
    (9)Very good
    5.9 miles from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA1 / 38
    (61)Very good
    3.0 miles from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 10
    1.7 miles to KY Horse Park1 / 18
    (67)Very good
    6.4 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Adorable 2 bedroom, 3 bathroom townhouse downtown with reclaimed boutique  decor1 / 25
    (53)Excellent
    1.0 miles from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Private Lake/Farm Retreat1 / 16
    (40)Excellent
    12.4 miles from Rupp Arena
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Lexington, Kentucky
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
    King bed. 2 bedroom. Pet-friendly. Fenced back yard. Near Downtown.1 / 34
    (24)Excellent
    1.8 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Charming Kentucky Cottage1 / 16
    (23)Excellent
    1.7 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-641 / 40
    (27)Excellent
    6.9 miles from Rupp Arena
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Lexington, Kentucky
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    **Bluegrass Getaway**1 / 9
    (3)Excellent
    2.2 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Stylish Kentucky Hospitality1 / 31
    (8)Excellent
    0.7 miles from Rupp Arena
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Lexington, Kentucky
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
    Luxury Updated Chevy Chase Home - Close to UK1 / 29
    (84)Excellent
    1.6 miles from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms1 / 11
    (23)Excellent
    0.9 miles from Rupp Arena
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
    **Brand New Cozy Apartment|Close to Everything**1 / 9
    (9)Excellent
    2.3 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    The Black Bear Lodge1 / 29
    (27)Very good
    0.3 miles 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
    Comfortable Family Home1 / 18
    (76)Excellent
    3.0 miles from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Lexington, Kentucky
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 13
    Kimball Suite-3 bedroom / 2 Bathroom1 / 49
    (38)Very good
    0.3 miles 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
    (87)Excellent
    3.6 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lexington, Kentucky
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Kathy's Place Near downtown/Rupp, UK, Horse Park1 / 34
    (18)Excellent
    1.3 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    JW's LOFT Near downtown/Rupp Arena, UK, Horse Park1 / 32
    (18)Very good
    1.3 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    The Kentucky Bourbon Suite1 / 49
    (56)Excellent
    0.3 miles from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Private Apartment in Downtown Lexington1 / 7
    (51)Excellent
    0.3 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Bungalow Bill's near downtown Keeneland Horse Park1 / 50
    (16)Excellent
    1.7 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lexington Apt. with parking & private entrance Preview listing1 / 10
    (52)Excellent
    5.8 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Historic Downtown Private Room and Bath1 / 11
    (35)Excellent
    0.7 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Lexington, Kentucky
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    4.1 miles from Rupp Arena
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Adorable 2 Bedroom Walk-Out with Theatre and Game Room1 / 49
    (8)Excellent
    6.5 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    0.4 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Luxury 5BR/4BA Updated Home In The Heart Of Lexington1 / 36
    (46)Excellent
    3.3 miles from Rupp Arena
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
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    Location Information
    Lexington, Kentucky
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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