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Results: 44 Rentals

  • Charming Louisville Gem: Walk to Restaurants!
    From $330 per night (USD)

    VRBO

    Charming Louisville Gem: Walk to Restaurants!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    2,502 Sq Ft | WFH Friendly | Sun Porch Discover the best of the Bluegrass State from this 4-bedroom, 2-bath vacation re ...

    From $330 per night (USD)

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    Details
  • Retro Chic Private Highlands Getaway
    From $116 per night (USD)

    Expedia

    Retro Chic Private Highlands Getaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Relax and enjoy this brand new retro chic private getaway in the Highlands. This one bedroom full bath with a jetted ba ...

    From $116 per night (USD)

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    Details
  • Charming Highlands Carriage House (2 beds\/2bath)
    From $129 per night (USD)

    VRBO

    Charming Highlands Carriage House (2 beds\/2bath)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The location of our Carriage House is perfect. It is private apartment on our property (guest house) in a beautiful qui ...

    From $129 per night (USD)

    VRBO

    Details
  • Beautiful Highlands Home Derby Weekend
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    Expedia

    Beautiful Highlands Home Derby Weekend

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Beautiful 4 bedroom, 3 1/2 bathroom home available for Derby weekend!! Sleeps 8-10! Location Location Location!! Two mil ...

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  • 3 Bedroom Home in the Highlands, close to everything
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    VRBO

    3 Bedroom Home in the Highlands, close to everything

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Recently renovated 2400 square foot home with covered porch overlooking garden. Master has soaking tub and separate show ...

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  • Perfect Derby Home, Charming Highlands Colonial
    From $848 per night (USD)

    VRBO

    Perfect Derby Home, Charming Highlands Colonial

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Thank you for your interest! Our beautiful home in the historic Highlands is currently available for rent. Our convenien ...

    From $848 per night (USD)

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    Details
  • Lovely Gem in the Vibrant Highlands close to it all!
    From $667 per night (USD)

    VRBO

    Lovely Gem in the Vibrant Highlands close to it all!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Boulevard Napoleon one of the most beautiful Tree-lined streets in the Highlands, this charming 100-year-old ...

    From $667 per night (USD)

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  • Charming home in the Highlands for Derby Weekend!
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    Charming home in the Highlands for Derby Weekend!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Warm and welcoming home perfect for a visit to the great city of Louisville. Stay in and enjoy all the amenities of a c ...

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  • Derby Rental in Cherokee Park Steps from Famous Barnstable Brown Party
    From $1045 per night (USD)

    VRBO

    Derby Rental in Cherokee Park Steps from Famous Barnstable Brown Party

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    What makes this rental unique is the amount of space, proximity to both the tracks and adored Cherokee Park (~25 minutes ...

    From $1045 per night (USD)

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  • Bourbon Mansion 3 Story Walk to Restaurants Park
    From $1050 per night (USD)

    Expedia

    Bourbon Mansion 3 Story Walk to Restaurants Park

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    16

    *Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required ...

    From $1050 per night (USD)

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  • Alfesco - Walkable Highlands Guesthouse
    From $175 per night (USD)

    VRBO

    Alfesco - Walkable Highlands Guesthouse

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    2

    Summary: Alfresco's private and peaceful guesthouse in the heart of the Highlands is within walking distance to some of ...

    From $175 per night (USD)

    VRBO

    Details
  • Kentucky at its best! Historical meets modern amenities!
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    Kentucky at its best! Historical meets modern amenities!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    A circa 1935 newly-remodeled family home in the heart of the Highlands has a luxurious new kitchen, 4 levels of roomy co ...

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  • Remodeled Designer Home Near Restaurants, Parks & Track
    From $3877 per night (USD)

    VRBO

    Remodeled Designer Home Near Restaurants, Parks & Track

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Nestled on the corner of one of Louisville's most desired streets, this newly remodeled home features charming cottage a ...

    From $3877 per night (USD)

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  • Beautiful home in the highlands of Louisville Kentucky
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    Beautiful home in the highlands of Louisville Kentucky

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The main floor has a formal living room that opens up to the dining room and remodeled kitchen. Also on the main flo ...

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  • NEW 2 KIngs Highlands Retreat
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    NEW 2 KIngs Highlands Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy the charm of our Highlands neighborhood with all-new everything. Luxurious spa-like retreat brand new stainless st ...

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  • Spacious 2B\/1BA in Buzzing Louisville Neighborhood
    From $134 per night (USD)

    Expedia

    Spacious 2B\/1BA in Buzzing Louisville Neighborhood

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    NEWLY RENOVATED 2 Bed 1 Bath upper level of duplex is perfect for small groups, couples, or business travelers. Upon arr ...

    From $134 per night (USD)

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  • DELETE this listing
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    VRBO

    DELETE this listing

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Cancel this listing- Cancel this listing Cancel this listing- Cancel this listing Cancel this listing- Cancel this listi ...

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    Details
  • Quiet Upper Highlands 1 Min to Bardstown Rd.
    From $209 per night (USD)

    Expedia

    Quiet Upper Highlands 1 Min to Bardstown Rd.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your dream vacation home in the heart of Louisville! Experience the best of both worlds with our prime locati ...

    From $209 per night (USD)

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    Details
  • Bourbon House 4 - The Wellingmoor - Hot Tub
    From $245 per night (USD)

    VRBO

    Bourbon House 4 - The Wellingmoor - Hot Tub

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Spread out and relax at The Wellingmoor, the 4th addition to the Louisville Bourbon House collection of properties. Sout ...

    From $245 per night (USD)

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    Details
  • Magnolia House Walk 2 Brewery\/Bars\/Restaurants
    From $460 per night (USD)

    Expedia

    Magnolia House Walk 2 Brewery\/Bars\/Restaurants

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    10

    * Superhost property * 2400 sq ft 2nd + 3rd floor space *Private patio w BBQ * 65" 4K TV + Wifi + Bedroom TV's * Ons ...

    From $460 per night (USD)

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  • ⁂Magnolia House \/Walk 2 Grocery\/Park\/Brewery⁂
    From $254 per night (USD)

    VRBO

    ⁂Magnolia House \/Walk 2 Grocery\/Park\/Brewery⁂

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    * Superhost property * 1,400 sq ft 1st floor space, open weekdays * Private patio w BBQ * 65" 4K TV's + Wifi * Onsi ...

    From $254 per night (USD)

    VRBO

    Details
  • Highlands Derby Home
    From $4120 per night (USD)

    Expedia

    Highlands Derby Home

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    9

    This is our beautiful personal home that we are making available to Derby guests. We are in a gorgeous, peaceful, safe, ...

    From $4120 per night (USD)

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    Details
  • Spacious House walking distance to Bardstown Road
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    Spacious House walking distance to Bardstown Road

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Spacious 3 bed 2.5 bath house 2,400 square feet walking distance to Bardstown Rd. Beautiful views overlooking a quiet ne ...

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  • My Old Kentucky House
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    My Old Kentucky House

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    This beautiful home has been newly remodeled and the basement has brand new bedrooms, bathroom, and kitchenette! Your D ...

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  • Derby Rental - PERFECT LOCATION!
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    Derby Rental - PERFECT LOCATION!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our impeccable2 story 2+ bedroom 1.5 bathroom Cape Cod house is ready to host you for your Derby experience. Located ~1 ...

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  • Fabulous Highlands house: 8 min to track: walk to restaurants
    From $448 per night (USD)

    VRBO

    Fabulous Highlands house: 8 min to track: walk to restaurants

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    WIN PLACE SHOW! You hit the trifecta with this highlands home! Perfect location to everything. 8 minutes to track, 8 ...

    From $448 per night (USD)

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  • Chic 4BR Farmhouse Near Historic Bardstown Road
    From $496 per night (USD)

    VRBO

    Chic 4BR Farmhouse Near Historic Bardstown Road

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Farmhouse Near Historic Bardstown Road by BNB Louisville. Welcome to our enticing Highlands retreat nestled in the vibra ...

    From $496 per night (USD)

    VRBO

    Details
  • Cozy, great LOCATION, smoke FREE!
    From $302 per night (USD)

    Expedia

    Cozy, great LOCATION, smoke FREE!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Location Location Location! 7 miles from Churchill Downs (14 minutes) 7 miles to KY Expo Center (13 minutes) 7 miles to ...

    From $302 per night (USD)

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  • Spacious 3 bedroom home
    From $1957 per night (USD)

    VRBO

    Spacious 3 bedroom home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This home has 3,800 sq feet with 3 bedrooms, 12-15 minutes driving to downtown Louisville. Close to restaurants, pubs, ...

    From $1957 per night (USD)

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    Details
  • Grand Loft in the Heart of the Highlands #4
    From $107 per night (USD)

    VRBO

    Grand Loft in the Heart of the Highlands #4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    It is MANDATORY that the guest is either a medical professional(Travel Nurse ) or Co-Operate person. We need proof of c ...

    From $107 per night (USD)

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  • Grand Two Bedroom in the heart of the highlands
    From $109 per night (USD)

    VRBO

    Grand Two Bedroom in the heart of the highlands

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    It is MANDATORY that the guest is either a medical professional(Travel Nurse ) or Co-Operate person. We need proof of ...

    From $109 per night (USD)

    VRBO

    Details
  • Grand Modern Apartment in the Heart  of Highlands
    From $101 per night (USD)

    VRBO

    Grand Modern Apartment in the Heart of Highlands

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    It is MANDATORY that the guest is either a medical professional(Travel Nurse ) or Co-Operate person. We need proof of ...

    From $101 per night (USD)

    VRBO

    Details
  • Family Friendly Derby City Getaway - minutes from track and festival grounds
    From $658 per night (USD)

    VRBO

    Family Friendly Derby City Getaway - minutes from track and festival grounds

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Family Friendly Derby City Getaway that sleeps 12. Minutes from Churchill Downs, the Festival Grounds, and parking for t ...

    From $658 per night (USD)

    VRBO

    Details
  • Newly Remodeled home|2 King Beds|Lounge |Game Room
    From $428 per night (USD)

    Expedia

    Newly Remodeled home|2 King Beds|Lounge |Game Room

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Welcome to Louisville, where Southern charm meets thrilling adventures! Immerse yourself in the excitement of t ...

    From $428 per night (USD)

    Expedia

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  • Bardstown Beauty
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    Bardstown Beauty

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Bring the whole family to this great place with lots of room for fun. Nestled in the upper highlands, this home is minut ...

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  • Highlands Haven
    From $1725 per night (USD)

    Expedia

    Highlands Haven

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Five miles from Churchill Downs! Charming and beautifully decorated 100-year-old Craftsman, this 4 bedroom, 3 bathroom h ...

    From $1725 per night (USD)

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  • Cozy & Spacious Apt | King Beds & Free Parking
    From $97 per night (USD)

    VRBO

    Cozy & Spacious Apt | King Beds & Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Welcome to the coveted Highlands neighborhood! This cozy, spacious apartment offers the perfect blend of comfor ...

    From $97 per night (USD)

    VRBO

    Details
  • Modern Highlands Home
    From $1082 per night (USD)

    Expedia

    Modern Highlands Home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a modern home in the heart of the sought after Highlands neighborhood. If it it Derby season, You will be two blo ...

    From $1082 per night (USD)

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  • Cozy Derby Home
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    Cozy Derby Home

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    his home is conveniently located just 7 miles (15 minutes) away from Churchill Downs. The backyard of this place is a pe ...

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  • Derby and PGA Championship House - Amazing location!
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    Derby and PGA Championship House - Amazing location!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Located less than 15 mins from Churchill Downs, less than 2 miles from the Barnstable-Brown Derby-Eve party, less than 5 ...

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  • Modern 3-bedroom house with pool, spa, and infrared sauna in the Highlands
    From $171 per night (USD)

    VRBO

    Modern 3-bedroom house with pool, spa, and infrared sauna in the Highlands

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    **Welcome to Seneca Vista Cabana – Your Perfect Highlands Retreat!** Nestled in the scenic Highlands near Seneca Park, ...

    From $171 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom! Hottub, Walking distances to Food, Shops, & Bars!
    From $550 per night (USD)

    VRBO

    Charming 3-bedroom! Hottub, Walking distances to Food, Shops, & Bars!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    11

    HOT TUB! Enjoy the convenience of this centrally located cozy, 3/4 bed room townhome. Free, Private off street parking ...

    From $550 per night (USD)

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    Details
  • 3BR Home Near EVERYTHING | King Beds | Game Room
    From $507 per night (USD)

    VRBO

    3BR Home Near EVERYTHING | King Beds | Game Room

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Louisville, where Southern charm meets thrilling adventures! Enjoy private access to our inviting home, perfe ...

    From $507 per night (USD)

    VRBO

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  • Charming 4-bedroom house in the upper Highlands neighborhood in Louisville
    From $1451 per night (USD)

    Expedia

    Charming 4-bedroom house in the upper Highlands neighborhood in Louisville

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Nestled in Louisville, this delightful house boasts 4 bedrooms including 1 king bed, 2 queen beds, and 1 bunk bed. With ...

    From $1451 per night (USD)

    Expedia

    Details