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Highlands Holiday Rentals

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    Travellers to Louisville are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    13 Matching Rentals in LouisvilleView all 57 rentals
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    Lovely Highlands Home, Steps to Restaurant Row!1 / 33
    (5)Excellent
    Highlands
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Carriage House, First Floor1 / 5
    (1)Excellent
    Highlands
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Highlands
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 bed/2.5 bath Historic District  Luxury Townhouse1 / 15
    (9)Excellent
    Highlands
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2015
    Even better than the pictures and description! Our family of six had a great week at the townhouse. Really well set up and stocked kitchen made cooking easy- but we still ate...
    Reviewed 2 December 2013
    Bud has this hospitality thing all wrapped up in a warm comfy blanket! The cabin was warm and welcoming and little personal touches make for a perfect experience. We had plans...
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    About this property
    Perfectly located townhouse in Louisville's premier historic district, The Cherokee Triangle. 200 feet to great restaurants, with dozens more restaurants, cafes, shops and clubs within a five minute walk. The townhouse is 1550 square feet. On the first floor is the living room, dining area, fully...
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    Louisville, Kentucky 40204
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Penthouse Apartment1 / 15
    (2)Excellent
    Highlands
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Sauna
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2014
    My family and I stayed in Ross Manor for 7 days during my daughter's Acrobatics competition. It was the perfect spot for enjoying the Cherokee District and being close to the...
    Reviewed 12 July 2014
    The "penthouse" is amazing...Terri and David are superb hosts. If you are looking for an absolutely relaxed stay in Louisville, this is the place. You will be within...
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    About this property
    Very quiet, entire third floor of 1897 mansion. A roomy 1350 sq. ft consisting of three bedrooms and one bath. Completely furnished; linens, kitchenware, etc. Free use of laundry room in basement and courtyard with outdoor dining and barbecue for all manor house tenants. Great for long term stays...
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    Louisville, Kentucky 40204
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Large Historic Home, Walk to Dinner, parks, cafes!1 / 33
    (4)Excellent
    Highlands
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Parking
    • Washer
    • Patio
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    Great house@ fabulous location!a bit pricey. But worth it. Accommodated all of our guests and finding good restaurants was easy!
    Reviewed 29 November 2017
    Very spacious, lovely home in a great neighborhood. Plenty of room for our large family. Great outdoor space in the back, and also a nice deck on second floor. My wife and I...
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    About this property
    Spacious, beautiful home in the city's premier historic neighborhood, the Cherokee Triangle. Located just 1/2 block off 'Restaurant Row' (Baxter Ave/Bardstown Rd), the home is a 5 minute walk to great restaurants, cafes, shops and nightclubs. With six bedrooms and five full baths, the 5000 sq....
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    Louisville, Kentucky 40204
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    6 Bedroom Italianate Mansion in Historic Zone1 / 27
    (9)Excellent
    Highlands
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2018
    We came in with a group for a local conference, and found that this house worked very well for our needs. The 6 of us had way more than enough space, and really enjoyed the open...
    Reviewed 27 September 2018
    The house is gorgeous - and so well decorated! There is a staggering amount of space and the Highlands location really can't be beat. This is a lovely place to stay and a...
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    About this property
    Historic Mansion with all modern updates and a fabulous location! 6 bedroom, 5 bath house built in 1882 in a folk Italianate style with 12 foot ceilings, 10 foot tall windows, original crystal chandeliers and hardwood floors with 6000 square feet of living space. 5 miles from Churchill Downs...
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    Location Information
    Louisville, Kentucky 40204
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Highlands
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully furnished condo overlooking one-of-a-kind stainless steel pool. Approximately 725 square feet with an enclosed tiled patio. All utilities including wireless Internet, cable TV as well as free laundry access.One on-site parking space available with unit. Great for Derby visits as well as long...
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    Location Information
    Louisville, Kentucky 40204
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Highlands
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully furnished condo on second floor overlooking one-of-a-kind stainless steel pool. Approximately 725 square feet with an enclosed tiled patio. All utilities including wireless Internet, cable TV as well as free laundry access.One on-site parking space available with unit. Great for Derby visits...
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    Location Information
    Louisville, Kentucky 40204
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Carriage House-Second Floor1 / 7
    (1)Excellent
    Highlands
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 October 2014
    If you know Louisville, than it is easy to explain how delightful the area and the carriage house is. It is located one block from the great restaurants, shops, coffee houses...
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    About this property
    Fully furnished second floor of Carriage House located in the historic neighborhood of Cherokee Triangle. The original caretaker's fireplace mantel is still there after 116 years and so is the original wood floors. The hay loft was closed in about 1964 and the entire floor was renovated three...
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    Location Information
    Louisville, Kentucky 40204
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Highlands
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning home has just undergone a complete remodel. Lovely original details were kept and every modern luxury added. Over 3700 square feet of living space with an attached garage and additional off street parking for up to 4 cars. The home has five bedrooms and five bathrooms with bedding...
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    Location Information
    Louisville, Kentucky 40204
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Highlands
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 4 BR 2.5 bath 110 yr old home has 2400 square feet & is just 3.5 BLOCKS from Bardstown Road, the main restaurant/bar district. Coffee shops, book stores, the city's hippest restaurants and bars, Cherokee Park...all the amenities you could want within walking distance! We can provide air...
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    Location Information
    Louisville, Kentucky 40204
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Highlands
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great contemporary decor in this turnkey furnished, includes all utilities, internet (WiFi) and basic cable TV. Ideal for corporate individual desiring extended stay in Louisville area, or just someone that wants to stay in this great unit in a great location. Located on desirable Historic...
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    Location Information
    Louisville, Kentucky 40204
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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