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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 March dates now. Secure your vacation rental today, and have the perfect trip.
    All 326 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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    Pet friendly
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    Smoking allowed
    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
    'The Guest House', Located on a 300 acre horse farm.1 / 26
    (4)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
    1900 Home Just Restored to last a century1 / 29
    (7)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 / 29
    (19)Excellent
    2.0 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    5.5 kilometres from Rupp Arena
    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
    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
    Spacious updated 4 bedroom house near Kentucky horse park1 / 29
    (26)Excellent
    6.1 kilometres from Rupp Arena
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful Woodward Heights Townhouse!1 / 24
    (21)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
    Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech1 / 12
    (55)Excellent
    0.4 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    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
    (12)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
    Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA1 / 29
    (74)Very good
    4.9 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 10
    Perfect House for Breeders Cup / Keeneland1 / 23
    (1)Excellent
    3.3 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Lake/Farm Retreat-Getaway1 / 15
    (43)Excellent
    20.0 kilometres from Rupp Arena
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    **Bluegrass Getaway**1 / 8
    (4)Excellent
    3.6 kilometres 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 / 29
    (9)Excellent
    1.1 kilometres from Rupp Arena
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
    Luxury Bungalow | 5 Star Location | Close to UK & Keeneland | Outdoor Patio | Wa1 / 29
    (91)Excellent
    2.4 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    **Brand New Cozy Apartment|Close to Everything**1 / 8
    (9)Excellent
    3.8 kilometres 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
    Comfortable Family Home1 / 18
    (83)Excellent
    4.9 kilometres from Rupp Arena
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 13
    Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway1 / 8
    (97)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
    The Kentucky Bourbon Suite1 / 29
    (65)Excellent
    0.6 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Lexington Apt. with parking & private entrance Preview listing1 / 10
    (63)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 Entry, Room and Bath1 / 14
    (37)Excellent
    1.2 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Fairyhouse Hall. Quintessential Kentucky Bourbon + Horse Experience w/ Chef.1 / 23
    (12)Excellent
    17.2 kilometres from Rupp Arena
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location1 / 24
    (95)Excellent
    0.6 kilometres from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    3 Bdr/3 Bath House in Andover Convenient to All of Lexington1 / 29
    (209)Excellent
    8.6 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Cheerful and Cozy in the Heart of Chevy Chase!1 / 17
    (60)Excellent
    2.5 kilometres from Rupp Arena
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    GuestHouse on Kentucky Working Thoroughbred Horse Farm1 / 11
    (63)Excellent
    5.4 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 3
    8.2 kilometres from Rupp Arena
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
    1.7 miles to KY Horse Park1 / 17
    (73)Very good
    10.3 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 3 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 3
    Adorable 2 bedroom, 3 bathroom townhouse downtown with reclaimed boutique  decor1 / 25
    (53)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
    King bed. 2 bedroom. Pet-friendly. Fenced back yard. Near Downtown.1 / 29
    (32)Excellent
    3.0 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Charming Kentucky Cottage1 / 15
    (28)Excellent
    2.7 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 3 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 3
    KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-641 / 40
    (27)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
    1.5 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    The Black Bear Lodge1 / 29
    (35)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
    The Kimball Suite-3 bedroom/2 Bathroom1 / 29
    (42)Very good
    0.6 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Kathy's Place - PET FEE ADDITIONAL CHARGE1 / 29
    (18)Excellent
    2.2 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    1.9 kilometres from Rupp Arena
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    JW's LOFT - PET FEE ADDITIONAL CHARGE1 / 29
    (22)Excellent
    2.2 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Private Apartment in Downtown Lexington1 / 7
    (57)Excellent
    0.4 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Bungalow Bill's - PET FEE ADDITIONAL CHARGE1 / 50
    (20)Excellent
    2.8 kilometres from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Glamorous Luxury Home | Close to Downtown | Hot Tub | Outdoor Porch & Patio | Te1 / 46
    (56)Excellent
    5.3 kilometres from Rupp Arena
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Balcony
    • Internet Access
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    3.1 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • DVD Player
    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 1
    2 Connecting Suites with Three Beds and Two Sofabeds at a Full Service Hotel by1 / 29
    (1)Very good
    5.8 kilometres from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 10
    1.6 kilometres from Rupp Arena
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Check-in Check-out
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    Amenities & Details
    • Balcony
    • Washer
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    3.1 kilometres from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    homeaway logo
    Check-in Check-out
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    Amenities & Details
    • Housekeeping Included
    • Internet Access
    • Air Conditioning
    • Shared Indoor Pool
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    1
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