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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 September dates now. Secure your vacation rental today, and have the perfect trip.
    All 73 Rentals in Lexington
    15 Min to Keeneland/KY Horse Park/Red MileRacetrack/Airport/Downtown Lexington1 / 33
    (1)Excellent
    4.0 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Bluegrass Calling1 / 20
    (1)Excellent
    4.2 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3.6 miles from Rupp Arena
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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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    Reviewed May 17, 2018
    Stayin in this part of Lexington was different for us....then we saw this very unique row house and just had to try it....what a neat experience....close to Rupp Arena and...
    Reviewed May 16, 2018
    I can easily say that this was one of my favorite stays so far. The communication was perfect. He was attentive, helpful and easy to reach. The checkin/out process was simple...
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
    0.3 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This is a 3 bed / 2 bath, with full kitchen. It is just two blocks from downtown, Rupp Arena, Town & Branch Distillery, and close to the Red Mile, the Kentucky Horse Park and the UK Campus. Perfect for large groups visiting the Bourbon Trail, events at Rupp, Keeneland, or just looking for a place...
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    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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    Reviewed May 27, 2019
    We came here for a graduation. The graduation was right across the street. Cabin is beautiful and held all nine of us
    Reviewed March 12, 2019
    This is the best little place! I can't imagine staying anywhere else in Lexington. The cabin is located in the perfect spot. You can walk anywhere in town that you'd...
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    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
    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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    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    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
    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
    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
    3.5 miles from Rupp Arena
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3.9 miles 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 8 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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    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
    0.2 miles 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
    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
    2.9 miles 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
    Comfort & Convenience in Downtown Lexington1 / 12
    (1)Excellent
    0.6 miles from Rupp Arena
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed April 13, 2019
    Located next to Transylvania University, convenient to downtown. Clean, spacious apartment with basic amenities. Comfortable and cozy. Drea was an amazing host. Definitely...
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    About this property
    'The McGinnis House' built in 1890's, this Victorian Era beauty was home to Asa McGinnis, the owner of the local neighborhood grocery store. While preserving the historic charm, we painstakingly renovated the entire building from top to bottom. Now upgraded with all modern comforts and amenities...
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4.6 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Newly renovated apartment in our home in a quiet upscale Lexington neighborhood. We are 5 minutes from the airport and Keeneland. You are close to dining and entertainment, but still able to relax and unwind after exploring the Bluegrass area, You have a private entrance to the apartment through...
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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
    4.3 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    1600 sqft home 3 bedroom/2 bathroom home. This home is specifically tailored for you and used only for a rental home. There are no steps in the home. There is sleeping and dining room for 10. The house is fully furnished for all your traveling needs. Attractions: Distance Kentucky horse...
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Bourbon Barrel Suite1 / 44
    (7)Excellent
    0.3 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
    KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-641 / 40
    (21)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
    (2)Excellent
    0.7 miles from Rupp Arena
    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Lexington, Kentucky
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 16
    Luxury Updated Chevy Chase Home - Close to UK1 / 16
    (35)Excellent
    1.5 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
    Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms1 / 11
    (8)Excellent
    0.9 miles 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
    Fabulous 1880 Victorian 'castle' in North End downtown Lexington1 / 22
    (5)Excellent
    1.3 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
    **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
    Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location1 / 24
    (51)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
    3 Bdr/3 Bath House in Andover Convenient to All of Lexington1 / 37
    (169)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
    Spacious updated 4 bedroom house near Kentucky horse park1 / 22
    (10)Excellent
    3.8 miles from Rupp Arena
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Lexington, Kentucky
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    The Black Bear Lodge1 / 28
    (8)Very good
    0.4 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
    Cheerful and Cozy in the Heart of Chevy Chase!1 / 15
    (14)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
    Central Located Lexington Home-Newly Remodled1 / 23
    (9)Very good
    2.3 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    A THOROUGHBRED Experience minutes to Keeneland, Horse Park, Fasig &DT Lexington!1 / 48
    (15)Excellent
    4.3 miles from Rupp Arena
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Comfortable Family Home1 / 18
    (49)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
    (16)Excellent
    0.3 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway1 / 8
    (49)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
    Beautiful Woodward Heights Townhouse!1 / 25
    (9)Very good
    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
    CLOSE TO UK FOOTBALL, DOWNTOWN, RUPP ARENA, UK CAMPUS, BOURBON TRAIL1 / 34
    (16)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
    Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech1 / 15
    (16)Very good
    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
    Guest House on Kentucky Working Thoroughbred Horse Farm1 / 12
    (25)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
    (10)Excellent
    0.3 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
    Welcome to your new Hartland home!1 / 15
    (5)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 / 39
    (19)Excellent
    3.0 miles from Rupp Arena
    2 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Lexington, Kentucky
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 11
    Where City & Woods Collide!1 / 30
    (13)Very good
    5.1 miles from Rupp Arena
    5 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Lexington, Kentucky
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 13
    1.7 miles to KY Horse Park1 / 18
    (45)Very good
    6.4 miles from Rupp Arena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lexington, Kentucky
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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