Strathmoor Village Rentals
- 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)VRBO
- 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)Expedia
- 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
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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 ...
Click For PricingExpedia
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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 ...
Click For PricingVRBO
- 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)VRBO
- 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)VRBO
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Expedia
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 ...
Click For PricingExpedia
- 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)VRBO
- 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)Expedia
- 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
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Expedia
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 ...
Click For PricingExpedia
- 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)VRBO
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Expedia
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 ...
Click For PricingExpedia
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VRBO
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 ...
Click For PricingVRBO
- 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)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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
- 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)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
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Expedia
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 ...
Click For PricingExpedia
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VRBO
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 ...
Click For PricingVRBO
- 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)VRBO
- 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
- 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)Expedia
- 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)VRBO
- 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)VRBO
- 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
- 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
- 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
- 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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Expedia
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 ...
Click For PricingExpedia
- 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)Expedia
- 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
- 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)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- 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
- 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)VRBO
- 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
- 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