Strathmoor Village Rentals
From $370 per night (USD)VRBO
8 Mi to Kentucky Derby: Charming Louisville Gem
- 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 $370 per night (USD)VRBO
From $129 per night (USD)Expedia
Charming Highlands Carriage House 2 beds/2bath \nNO POOL
- 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)Expedia
From $737 per night (USD)VRBO
Lovely Gem in the Vibrant Highlands close to it all!
- Bedrooms:
- 2
- 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 $737 per night (USD)VRBO
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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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From $2570 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, and it's on ...
From $2570 per night (USD)VRBO
From $846 per night (USD)Expedia
Farmers Market, Brewery, Bardstown 2 Decks & Porch
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Beautifully renovated 100+ year old mansion in the heart of the Highlands neighborhood. • 6 Bedrooms, 5 Full bathroom ...
From $846 per night (USD)Expedia
From $104 per night (USD)VRBO
Alfesco - Walkable Highlands Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Alfresco's private and peaceful guesthouse in the heart of the Highlands is within walking distance to some of ...
From $104 per night (USD)VRBO
From $3231 per night (USD)VRBO
Remodeled Designer Home Near Restaurants, Parks & Track
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled on the corner of one of Louisville's most desired streets, this newly remodeled home features charming cottage a ...
From $3231 per night (USD)VRBO
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Beautiful home in the highlands of Louisville Kentucky
- Bedrooms:
- 1
- 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
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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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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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From $235 per night (USD)Expedia
Quiet Upper Highlands 1 Block to Bardstown Road
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Comfortable, spacious, conveniently located. Nestled in the sought-after Upper Highlands area, just one block from the l ...
From $235 per night (USD)Expedia
From $254 per night (USD)VRBO
Bourbon House 4 - The Wellingmoor - Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spread out and relax at The Wellingmoor, the 4th addition to the Louisville Bourbon House collection of properties. Sout ...
From $254 per night (USD)VRBO
From $363 per night (USD)Expedia
Magnolia House Walk 2 Brewery/Bars/Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
* Superhost property * 2400 sq ft 2nd + 3rd floor space *Private patio w BBQ * 65" 4K TV + Wifi + Bedroom TV's * Ons ...
From $363 per night (USD)Expedia
From $272 per night (USD)VRBO
⁂Magnolia House /Walk 2 Grocery/Park/Brewery⁂
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
* Superhost property * 1,400 sq ft 1st floor space, open weekdays * Private patio w BBQ * 65" 4K TV's + Wifi * Onsi ...
From $272 per night (USD)VRBO
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Derby Rental - PERFECT LOCATION!
- Bedrooms:
- 1
- 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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From $386 per night (USD)VRBO
Chic 4BR Farmhouse Near Historic Bardstown Road
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Farmhouse Near Historic Bardstown Road by BNB Louisville. Welcome to our enticing Highlands retreat nestled in the vibra ...
From $386 per night (USD)VRBO
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 $725 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 $725 per night (USD)VRBO
From $85 per night (USD)Expedia
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 $85 per night (USD)Expedia
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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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From $533 per night (USD)Expedia
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 $533 per night (USD)Expedia
From $1451 per night (USD)VRBO
Charming 4-bedroom house in the upper Highlands neighborhood in Louisville
- Bedrooms:
- 3
- 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)VRBO
From $882 per night (USD)Expedia
14 Beds Game Room Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
You've found it! This home is spacious and ready for your next trip. Huge kitchen, 2 family rooms on main floor, large b ...
From $882 per night (USD)Expedia
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Derby Dream 4-bedroom house with WiFi and AC in brilliant Louisville
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in 100 year old quiet neighborhood, Enjoy 2300 sq feet, 3 bedroom with extra in finished basement. With 4 queen ...
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From $200 per night (USD)Expedia
Charming 2-bedroom bungalow in desirable Louisville Highlands neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your Louisville adventure begins at this 2-bedroom bungalow. Nestled in a peaceful neighborhood, this quaint retreat off ...
From $200 per night (USD)Expedia
From $784 per night (USD)VRBO
Highlands House with King Bed and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Old charm mixed with modern amenities. We have two spacious bedrooms upstairs with a full bathroom where 6 guests can sl ...
From $784 per night (USD)VRBO
From $258 per night (USD)Expedia
Beautifully charming 3-BR house in the convenient Highlands area of Louisville
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This Louisville house boasts views of historic Bowman Field and all of its private planes. Enjoy 3 inviting bedrooms wit ...
From $258 per night (USD)Expedia
From $469 per night (USD)VRBO
The Reserve ~ 5BR Fun! Hot Tub, Fire Pit, Deck, Walkable To Bardstown Rd
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Your Highlands home-away-from-home! Gather in roomy, welcoming spaces, cook up meals together, then head out to explore ...
From $469 per night (USD)VRBO