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Holiday Rentals near Keeneland

4201 Versailles Rd, Lexington, Kentucky 40510-9648
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    Travellers to Lexington are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 50 Rentals in Lexington
    15 Min to Keeneland/KY Horse Park/Red MileRacetrack/Airport/Downtown Lexington1 / 33
    (1)Excellent
    4.4 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Bluegrass Calling1 / 20
    (1)Excellent
    3.6 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4.2 miles from Keeneland
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3.1 miles from Keeneland
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    3.8 miles from Keeneland
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Town home with private garage and backyard1 / 18
    (7)Excellent
    6.9 miles from Keeneland
    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 3 Bathrooms, Sleeps 2
    6.3 miles from Keeneland
    1 Bedroom, 2 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 10
    6.7 miles from Keeneland
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3.9 miles from Keeneland
    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
    3.5 miles from Keeneland
    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
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    4.2 miles from Keeneland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Charming cottage home sets on a quaint 20 acre farm with horses and a vineyard situated 10 minutes from downtown Lexington and Midway. You get to enjoy the best of both worlds with the city and the country. Accommodations are a quaint cottage guest house on the farm. Owners live in a main house on...
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Bourbon Barrel Suite1 / 44
    (8)Excellent
    5.7 miles from Keeneland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-641 / 40
    (21)Excellent
    12.4 miles from Keeneland
    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
    (38)Excellent
    6.3 miles from Keeneland
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms1 / 11
    (8)Excellent
    6.3 miles from Keeneland
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 7
    3 Bdr/3 Bath House in Andover Convenient to All of Lexington1 / 37
    (169)Excellent
    10.5 miles from Keeneland
    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
    (11)Very good
    5.8 miles from Keeneland
    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
    (15)Excellent
    6.4 miles from Keeneland
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Central Located Lexington Home-Newly Remodled1 / 23
    (9)Very good
    5.3 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Kimball Suite-3 bedroom/2 Bathroom1 / 49
    (18)Excellent
    5.7 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway1 / 8
    (49)Excellent
    9.0 miles from Keeneland
    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
    (9)Very good
    5.2 miles from Keeneland
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    CLOSE TO UK FOOTBALL, DOWNTOWN, RUPP ARENA, UK CAMPUS, BOURBON TRAIL1 / 34
    (16)Excellent
    6.8 miles from Keeneland
    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
    (16)Very good
    5.4 miles from Keeneland
    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
    8.7 miles from Keeneland
    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 / 38
    (13)Excellent
    5.5 miles from Keeneland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Welcome to your new Hartland home!1 / 15
    (5)Very good
    9.3 miles from Keeneland
    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
    (46)Very good
    7.1 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Bluegrass Belle Duplex1 / 28
    (27)Excellent
    7.5 miles from Keeneland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Adorable 2 bedroom, 3 bathroom townhouse downtown with reclaimed boutique  decor1 / 25
    (38)Excellent
    6.5 miles from Keeneland
    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
    7.3 miles from Keeneland
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Near UK, Horse Park, Keeneland, Rupp Arena, Downtown, Restaurants & Bars nearby1 / 30
    (11)Very good
    6.8 miles from Keeneland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Private Lake/Farm Retreat1 / 16
    (24)Excellent
    15.6 miles from Keeneland
    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 / 50
    (11)Excellent
    5.5 miles from Keeneland
    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
    (44)Excellent
    5.4 miles from Keeneland
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Beautiful historic home in the heart of horse country!1 / 18
    (9)Very good
    13.3 miles from Keeneland
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Unique! Near UK, Horse Park, Keeneland, Rupp, Downtown, Restaurants & Bars1 / 43
    (9)Excellent
    7.1 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lexington Apt. with parking & private entrance Preview listing1 / 10
    (16)Excellent
    4.9 miles from Keeneland
    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
    (10)Very good
    6.4 miles from Keeneland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Unique Townhome 2blocks from New Circle Rd. Close to downtown and EVERYTHING LEX1 / 43
    (16)Excellent
    8.8 miles from Keeneland
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Luxury 5BR/4BA updated home in heart of Lexington1 / 40
    (7)Excellent
    7.0 miles from Keeneland
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    4.7 miles from Keeneland
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Studio living has never been this convenient in Lexington! This well-equipped vacation rental will treat you with everything needed for a relaxing trip to a Kentucky gem. Just a short distance from the University of Kentucky, this Kentucky gem lets you attend events and explore the campus, then...
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    Lexington, Kentucky
    Condo/Apartment - 1 Bathroom, Sleeps 2
    4.7 miles from Keeneland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Explore Lexington one day at a time while staying at this centrally located 2-bedroom, 1-bathroom apartment! Close to the UK campus, Rupp Arena, and Kroger Field, this vacation rental is ideal for anyone visiting the area for a sporting event, college graduation, or conferences. Embrace Kentucky...
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4.7 miles from Keeneland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore Lexington from the comfort of this 1-bedroom 1-bathroom vacation rental minutes away from the University of Kentucky. Well-appointed with a full kitchen, Smart TV, and a laptop-friendly workspace, this modern apartment makes it easy to take on the day in Lexington. Treat yourself to a trip...
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    Lexington, Kentucky
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.6 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    From watching galloping thoroughbreds to sipping your way along the Bourbon Trail or taking in a Cats game, you can do it all when you book this Lexington vacation rental. This 3-bedroom, 1.5-bath Bluegrass State bungalow is in the peaceful Gardenside neighborhood, just minutes from downtown and...
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Modern & Elegant Carriage House at Historic Warsaw1 / 15
    (7)Excellent
    9.2 miles from Keeneland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lexington, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    3 Bedroom Downtown Townhouse, Close to All!1 / 27
    (19)Very good
    5.5 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    4.6 miles from Keeneland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Start dreaming about greener pastures and head to this Lexington apartment, a retro retreat amidst the area’s top attractions. Spend the day touring the Thoroughbred Heritage Horse Farm and meeting elite-class racing enthusiasts, or head to the University of Kentucky to greet old friends or watch...
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3 Bed / 2 Bath Ranch On A Basement - You're Sure To Love This Updated Home!1 / 31
    (7)Excellent
    6.7 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Lexington, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Resort like in the heart of the very best neighborhood in the city1 / 17
    (4)Excellent
    3.9 miles from Keeneland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Lexington, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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