Cherokee Park Rentals
- From $69 per night (USD)
VRBO
Alfresco - Walkable Highlands Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Alfresco's private and peaceful guesthouse in the heart of the Highlands is within walking distance to some of Louisvill ...
From $69 per night (USD)VRBO
- Click For Pricing
Expedia
Victorian Era Bungalow Home adjacent to Tyler Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located on this highly desirable street that is bursting with color, 1824 Windsor Place in the Highlands is a must-see! ...
Click For PricingExpedia
- From $611 per night (USD)
VRBO
Ideal large vacation house for long weekend getaway or bourbon trail!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Fully furnished renovated historic home, perfect for hosting large groups for a fun-filled long weekend. Can accommodate ...
From $611 per night (USD)VRBO
- Click For Pricing
Expedia
Newly Renovated, Charming 1901 3Flr Craftsman in AMAZING Highlands Location
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Brand New listing! Newly renovated; a must-see house for your next vacation! You'll be in the heart of the Highlands His ...
Click For PricingExpedia
- From $378 per night (USD)
VRBO
Bourbon Suites -Foodies -Bourbon -2 Living Rooms
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
*Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required ...
From $378 per night (USD)VRBO
- From $646 per night (USD)
Expedia
Magnolia House Walk 2 Brewery\/Bars\/Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
* Superhost property * 2400 sq ft 2nd + 3rd floor space *Private patio w BBQ * 65" 4K TV + Wifi + Bedroom TV's * Ons ...
From $646 per night (USD)Expedia
- From $8160 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 $8160 per night (USD)VRBO
- From $713 per night (USD)
Expedia
*NEW* Highlands Down | 4BR 3BA KINGS | Sleep 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*BRAND NEW LISTING* The Highlands Down is the main floor condo in the uber-luxurious Grande Highland - a majestic Highla ...
From $713 per night (USD)Expedia
- Click For Pricing
VRBO
Bonny High~4BR | KING | w\/Epic Backyard + Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
"Bonny High" is an all new luxury destination located in the heart of Louisville's historic Highlands. Just steps from B ...
Click For PricingVRBO
- From $1402 per night (USD)
Expedia
Cinema w\/ 4 Suites @ Bungalou + Bourbon Bar
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 20
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $1402 per night (USD)Expedia
- From $319 per night (USD)
VRBO
Luxe Highlands Home! King Bed~Fire Pit~Yard Games
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover the ultimate blend of comfort and convenience in this beautifully remodeled 4-bedroom house in the heart of Lou ...
From $319 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Jungalou @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $295 per night (USD)Expedia
- Click For Pricing
VRBO
SchillHaus Level 3
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Park like setting in the heart of the city. Home located in hip Germantown on a half acre. Recently updated bedroom with ...
Click For PricingVRBO
- From $133 per night (USD)
VRBO
Classic Heart of Highlands! 3BR!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Stay and relax in a 3BR / 1 BA home in an unbeatable location! beautifully designed and fully renovated home perfect for ...
From $133 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Bluegrass Manor: Home & Apartment, LOCATION!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Welcome to your own slice of the Highlands! Walk right out the front doors to Bardstown Rd with over 50 local restaurant ...
From $900 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Amazing and Spacious 5BR Home!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Inside, you'll find modern amenities to make your stay as comfortable as possible. Stay entertained with a TV, stay cool ...
From $226 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Fully renovated 4BR Bardstown \/ Highlands!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Step outside your door and immerse yourself in the eclectic atmosphere of the Highlands, where you'll find local coffee ...
From $264 per night (USD)VRBO
- From $2200 per night (USD)
VRBO
Luxury home w\/ hot tub! Only 2 blocks from restaurants and bars! 4 mi from Derby
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
3,300 square foot luxury home located in historic Louisville (Highlands) neighborhood. Walkers’ paradise - only 2 block ...
From $2200 per night (USD)VRBO
- From $3457 per night (USD)
VRBO
Luxury Historic Estate
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Offering a lifestyle of unparalleled elegance and creativity, welcome to a one-of-a-kind, custom estate that seamlessly ...
From $3457 per night (USD)VRBO
- From $130 per night (USD)
Expedia
Brand new! Walk to all! +12 mins from Derby\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 9
Modern, funky, and extra comfy stay right on Bardstown Rd in the heart of the Highlands! Just steps away (literally, not ...
From $130 per night (USD)Expedia
- From $1485 per night (USD)
VRBO
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 $1485 per night (USD)VRBO
- From $72 per night (USD)
VRBO
Newly Remodeled Apt|King Beds|2BR|Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Located in the highly sought-after Highlands neighborhood, this newly renovated and spacious apartment will mak ...
From $72 per night (USD)VRBO
- From $920 per night (USD)
VRBO
Modern Highlands Home for Derby Weekend
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy Derby Weekend in a modern home in the heart of the sought after Highlands neighborhood. You'll be two blocks from ...
From $920 per night (USD)VRBO
- From $100 per night (USD)
Expedia
Charming Highlands Apartment: Heart of Louisville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy one of Louisville's most happening areas of town while relaxing in a charming and spacious second story duplex. Th ...
From $100 per night (USD)Expedia
- From $103 per night (USD)
VRBO
Central location! Historic neighborhood. Easy walk to shops and restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming historic home in Louisville's Crescent Hill neighborhood! This newly renovated 1,000 sq ft 1-bed ...
From $103 per night (USD)VRBO
- From $241 per night (USD)
Expedia
The Highlands Hideout
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a stylish experience at this centrally-located 2 bedroom,1 bathroom newer Apartment. Amazing location in the heart ...
From $241 per night (USD)Expedia
- From $120 per night (USD)
VRBO
New! Steps from everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Just steps away (literally, not like those others that are actually blocks away!) from numerous restaurants, bars, & sho ...
From $120 per night (USD)VRBO
- From $607 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 $607 per night (USD)VRBO
- From $110 per night (USD)
VRBO
Spacious Highlands Townhouse ~ 2BR\/2.5BA SLEEP 6
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Stay at our spacious 2BR/2.5BA townhouse in the heart of the Highlands, Louisville's most desirable neighborhood. The lo ...
From $110 per night (USD)VRBO
- Click For Pricing
Expedia
Edenside Suite 102 at The Bellwether Hotel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Immerse yourself in the era of Art Deco design when you settle into our ADA compliant Edenside Suite. Working ...
Click For PricingExpedia
- Click For Pricing
VRBO
Bellwether House Summ
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Bellwether House is a beautiful four-bedroom, four-bathroom home that boasts elegance and comfort. With its spa ...
Click For PricingVRBO
- From $3750 per night (USD)
VRBO
4BR, 3.5BA Beautiful & Bright Historic Home in Vibrant Neighborhood
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Beautifully updated 3 story Victorian home on a quiet street just a few blocks from Louisville’s bustling independent ba ...
From $3750 per night (USD)VRBO
- From $64 per night (USD)
VRBO
1 Bedroom 1 Bath Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our 1 and 2 bedroom condos are non-smoking, feature washers and dryers in your unit, queen size beds, a fully stocked ki ...
From $64 per night (USD)VRBO
- From $75 per night (USD)
VRBO
2 Bed 1 Bath with Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our 1 and 2 bedroom condos are non-smoking, feature washers and dryers in your unit, queen size beds, a fully stocked ki ...
From $75 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Historic three-level home in the Highlands
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled historic three level home, perfectly situated in the Highlands in walking distance to practically everyt ...
From $180 per night (USD)VRBO
- Click For Pricing
Expedia
The Golden Hour Suite 201 at The Bellwether Hotel
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Immerse yourself in the era of Art Deco design when you settle into the Golden Hour Suite. Working with the ex ...
Click For PricingExpedia
- From $667 per night (USD)
VRBO
Highlands Gem: Super Clean Guest Suite Sleeps 6, Plenty of Beds for Everyone!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Guest suite in our Cherokee Park duplex! Discover the charm of our super clean guest suite in the heart of Louisville' ...
From $667 per night (USD)VRBO
- From $665 per night (USD)
VRBO
Charming Highlands Duplex: Historic Elegance, Modern Comfort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Rent both levels of this Cherokee Park duplex! Welcome to our charming duplex in the heart of Louisville's Highlands n ...
From $665 per night (USD)VRBO
- From $823 per night (USD)
VRBO
Historic Highlands Home in Cherokee Park with or without optional Guest Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming duplex in the heart of Louisville's Highlands neighborhood, a vibrant area known for its unique ...
From $823 per night (USD)VRBO
- From $61 per night (USD)
VRBO
Bonnycastle Carriage House · Stellar Suites | Sunny Carriage House | Highlands
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This modern carriage house is cozy, clean and has the best location in the whole city. The apartment is right next to Ch ...
From $61 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
PGA Louisville 2024 - Lease my home
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 2
Your home for the PGA! My wife and I are opening our home to a family for the 10 days of the PGA. We have 4 bedrooms. 2 ...
From $1500 per night (USD)VRBO
- From $282 per night (USD)
Expedia
House on the Hill in Great Location w\/ Parking
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 14
This beautiful home was renovated in 2022 with our guests in mind. We paid special attention to certain details to make ...
From $282 per night (USD)Expedia
- From $64 per night (USD)
VRBO
1 Bedroom 1 Bathroom Furnished Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our 1 and 2 bedroom condos are non-smoking, feature washers and dryers in your unit, queen size beds, a fully stocked ki ...
From $64 per night (USD)VRBO
- From $75 per night (USD)
VRBO
2 Bedroom 1 Bathroom Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our 2 bedroom condos are non-smoking, feature washers and dryers in your unit, queen size beds, a fully stocked kitchen ...
From $75 per night (USD)VRBO
- Click For Pricing
VRBO
Cherokee Charmer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Set amidst Frederick Law Olmsted’s pristine Cherokee Park, this lovely home meets every desire for a relaxing stay. Feat ...
Click For PricingVRBO
- From $249 per night (USD)
VRBO
The Vernon House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space Welcome to The Vernon House! This home in the historic Crescent Hill neighborhood is within walking dis ...
From $249 per night (USD)VRBO
- From $1028 per night (USD)
VRBO
Prime Highlands 8BR 6BA KINGS |.Huge Yard-Parking
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
*BRAND NEW LISTING* Huge historic house, fantastic for groups!- Can sleep 18 guests MAX! Just steps to Bardstown Road in ...
From $1028 per night (USD)VRBO
- From $1174 per night (USD)
Expedia
Cinema Suites @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $1174 per night (USD)Expedia
- From $3032 per night (USD)
VRBO
Bungalou \"Ultimate Privacy: GOLD\" (Sleeps 50)
- Bedrooms:
- 19
- Bathrooms:
- 18
- Sleeps:
- 50
Summary: Sleeps up to 50!!! Bungalou's famous “Ultimate Privacy” GOLD Package awaits you at Louisville’s Premier “Stay-n ...
From $3032 per night (USD)VRBO
- From $4560 per night (USD)
VRBO
Celebrity Host Home. Best Derby Location!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The home has hosted A-list Hollywood celebrities in the past year for extended stays, it has glowing reviews, and the ho ...
From $4560 per night (USD)VRBO
- Click For Pricing
VRBO
Highlands Carriage House - Deer Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fully Furnished studio carriage house. Wifi and TVs provided. Living room with sleeper sofa, kitchen with large eat-in i ...
Click For PricingVRBO
- From $98 per night (USD)
Expedia
The Gallery Loft - Walk & Dine!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: This charming loft is a wonderful experience of its own, tastefully designed with a combination of vintage and ...
From $98 per night (USD)Expedia
- From $1373 per night (USD)
VRBO
Courtside - Highlands VIP 6BR 4BA Amenities Galore
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
BNB Louisville presents - Courtside is the Ville's hottest new sensation. We've taken all the best features from our pre ...
From $1373 per night (USD)VRBO
- From $107 per night (USD)
Expedia
Living on the Edge in the Highlands.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inhabit this private & spacious apartment in a historic duplex with comfort and personable charm. Spend a whole day expl ...
From $107 per night (USD)Expedia
- From $595 per night (USD)
VRBO
brand new LEGENDS LOUISVILLE - in the highlands!!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Alright! Alright! Alright! Welcome to Legends a throw back to some of the greatest musicians! A perfect spot on the stri ...
From $595 per night (USD)VRBO
- From $106 per night (USD)
VRBO
Secluded Mid Century Home in Crescent Hill on a 1\/2 acre in the city
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A four bedroom 2200 sq ft mid century home with period correct furnishings as well as vintage kitchen appliances. The ne ...
From $106 per night (USD)VRBO
- From $88 per night (USD)
VRBO
Cozy stay steps from everything!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just steps away (literally, not like those others that are actually blocks away!) from numerous restaurants, bars, & sho ...
From $88 per night (USD)VRBO
- From $363 per night (USD)
Expedia
Highlands Home w\/Private Parking, EV Charger, Large Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your home away from home in the heart of the Highlands. This charming 1,100 sq ft shotgun home is a private r ...
From $363 per night (USD)Expedia
- Click For Pricing
VRBO
Derby Winner!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Classic Painted Lady in the Cherokee Triangle, close to fine dining, nightlife, Cherokee Parkway, Golf Course and only 1 ...
Click For PricingVRBO
- From $475 per night (USD)
Expedia
Sleeps 8 Beautiful Home in desirable highland area 4.3 miles from track.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful Home in the heart of the Highlands and walking distance from Lakeside Country club. The home is a 4 Bedroom ...
From $475 per night (USD)Expedia
- From $538 per night (USD)
VRBO
Charming Home just off Bardstown Rd
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Our 2400 square-foot home is in the heart of the very popular Highlands neighborhood. It is within walking distance to s ...
From $538 per night (USD)VRBO
- From $171 per night (USD)
Expedia
Urban Oasis ~ Charming Cottage w\/Private Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
**NEW** This charming carriage house is the perfect getaway in the heart of the Highlands historic Cherokee Triangle. It ...
From $171 per night (USD)Expedia
- From $249 per night (USD)
VRBO
Centrally located, very walkable to bars and restaurants. 7 minutes to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This beautiful property is located in the heart of the highlands; it one of the most desirable neighborhoods in Louisvil ...
From $249 per night (USD)VRBO
- From $127 per night (USD)
Expedia
Derby Time! Highlands Home with View of Downtown Walkable.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This condo is in the heart of the popular Highlands neighborhood. Steps away from restaurants, bars, and shops on Baxte ...
From $127 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Historic Highlands Bungalow w\/ private backyard and firepit walk to Bardstown Rd
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Highlands! This 4 bedroom, 2 bath bungalow is centrally located in the historic Deer Park neighborhood. S ...
From $340 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Walk everywhere from this Modern Victorian
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the heart of the historic Cherokee Triangle neighborhood, this modern Victorian home is sure to make for a me ...
From $419 per night (USD)Expedia
- Click For Pricing
VRBO
Louisville Apartment ~ 5 Mi to Kentucky Derby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Craving a vacation to a new city? Add Louisville to your bucket list! With plenty of live entertainment, Southern charm, ...
Click For PricingVRBO
- Click For Pricing
Expedia
Walkable Louisville Studio Near Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Whether you’re looking for a relaxing retreat or a fun-filled vacation, you’ll find it here at this Louisville studio! T ...
Click For PricingExpedia
- Click For Pricing
VRBO
NEW 2 KIngs Highlands Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $244 per night (USD)
Expedia
Lovely 3BR\/1BA PRIME Location!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
NEWLY RENOVATED 3 Bed 1 Bath upper level of duplex is perfect for small groups, couples, or business travelers. Upon arr ...
From $244 per night (USD)Expedia
- From $741 per night (USD)
VRBO
Highlands Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Historic 4 bedroom home located in Cherokee Triangle. Just blocks from some of Louisville's best restaurants, pubs, shop ...
From $741 per night (USD)VRBO
- Click For Pricing
Expedia
New Signature Highlands Home- steps away from…
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our new to AirBNB Highlands home. Recently redecorated and updated, this home is steps away from many incredi ...
Click For PricingExpedia
- Click For Pricing
VRBO
10 minutes from everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Crescent Hill. Close to all things that make Louisville so great. Churchill Downs, Louisville Slugger, ...
Click For PricingVRBO
- From $178 per night (USD)
Expedia
Modern Louisville Apartment w\/ Furnished Deck
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Looking to enjoy a long stay or weekend getaway filled with Louisville luxury? Book a trip to this 2-bedroom, 1-bathroom ...
From $178 per night (USD)Expedia
- From $792 per night (USD)
VRBO
Highlands Magic! 5 bed, 2 ba, HOT TUB!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: **LOCALS MAY NOT BOOK WITHOUT PRIOR AUTHORIZATION FROM THE HOST** Just stop looking - Location? Magical Outd ...
From $792 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Louisville Home w\/ Hot Tub in The Highlands!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in the heart of the bustling Highlands neighborhood, this 3-bedroom, 2-bathroom house is the perfect destination ...
From $303 per night (USD)Expedia
- From $597 per night (USD)
VRBO
Highlands Derby City Dream ~ 6BR+Hot Tub Sleep 14
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
The ALL NEW "Highlands Derby City Dream" is a premier destination located in the heart of Louisville's historic Highland ...
From $597 per night (USD)VRBO
- Click For Pricing
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 $903 per night (USD)
VRBO
New! Big Shot Stables-6BD\/3BA - Hot Tub! Walkable!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Bring your group of Fillies and Stallions to Big Shot Stables! The Space: This beautiful gem is nestled JUST r ...
From $903 per night (USD)VRBO
- From $2000 per night (USD)
Expedia
Beautiful Derby, PGA, and Holiday Large Louisville home!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Five bedroom, remodeled home close to all of the Louisville favorites! Easy access to downtown, NuLu, FrankfortAvenue, t ...
From $2000 per night (USD)Expedia
- From $498 per night (USD)
VRBO
Bonnycastle Blue~Lux 6BR Epic Backyard + Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
"Bonnycastle Blue" is a prime stay and play destination for your large group. Located in the heart of Louisville's histo ...
From $498 per night (USD)VRBO
- From $138 per night (USD)
Expedia
2BR -HISTORIC & BRIGHT *PERFECT SPOT-FRANKFORT AVE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Walk to almost anything you need, restaurants, coffee shops, bookstores & boutique shops! Located in the trendy ...
From $138 per night (USD)Expedia
- From $2000 per night (USD)
VRBO
Highlands Gem w\/ hot tub, fire pit - walkable to Bardstown Rd
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Planning your Kentucky Derby trip? Hitting the Bourbon Trail? Planning some college visits? This gorgeous home will be a ...
From $2000 per night (USD)VRBO
- From $1150 per night (USD)
Expedia
⭐PERFECT for DERBY⭐ Heart of Restaurant District
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
--> Walk to Louisville's hottest restaurants and bars (Bardstown Rd) --> Walk to Louisville's most beautiful 400-acre pa ...
From $1150 per night (USD)Expedia
- From $2500 per night (USD)
VRBO
PGA - Historic Home in Cherokee Triangle Louisville - PGA
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
Live like a Louisvillian while attending the PGA Tournament in a 4500 square feet historic home in Cherokee Triangle. T ...
From $2500 per night (USD)VRBO
- From $3964 per night (USD)
Expedia
Beautiful 7000 square foot home with indoor pool located on Cherokee Park
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Just a minute walk from Cherokee Park and 12 minute drive to Churchill Downs our home is centrally located near shops an ...
From $3964 per night (USD)Expedia
- Click For Pricing
VRBO
Historic Home in the Highlands at Cherokee Park.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step back in time in a living area of elegant chandeliers, original decorated wood floors, and gilt-framed artwork. Taki ...
Click For PricingVRBO
- From $5000 per night (USD)
Expedia
Kentucky Derby or PGA Rental
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Best Location -9 miles from Churchill Downs Located in Louisville's most sought after neighborhood Located in the Heart ...
From $5000 per night (USD)Expedia
- From $7333 per night (USD)
VRBO
Derby City's Finest - Luxury Home With Guest House In Fabulous Location!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Located in Louisville's charming Crescent Hill neighborhood, this fully renovated historic home with it's newly construc ...
From $7333 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Vintage gem in the Highlands for group getaways with private workspace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this vintage gem conveniently located in the vibrant Highlands neighborhood. This modern 3-bed, 3-bath home i ...
From $350 per night (USD)VRBO
- From $878 per night (USD)
VRBO
New! Historic Home - Walkable! Hot tub! 5br
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Beautiful historic home nestled in our Highlands neighborhood - Louisville's arts and entertainment district! ...
From $878 per night (USD)VRBO
- From $100 per night (USD)
Expedia
Louisville Vacation Rental ~ 3 Mi to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ideally located just 3 miles away from downtown Louisville, this 2-bedroom, 2-bath vacation rental boasts all the modern ...
From $100 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Crescent Hill - great LOCATION! Smoke FREE!\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space LOCATION LOCATION!! This pet-free / smoke-free home is a 5 minute walk to many desirable Frankfort Aven ...
From $233 per night (USD)VRBO
- From $167 per night (USD)
Expedia
New! Charming City Condo! Walkable & Chic!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Beautiful and ready for your stay! This space is located in a building above a gentleman's boutique store. Nic ...
From $167 per night (USD)Expedia
- From $300 per night (USD)
VRBO
3 BR, 3 BA with Sauna, Pool, and Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Make some memories at this unique and family-friendly place. This 1900 square foot house, originally built in 1940, has ...
From $300 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Entire Home in the Highlands on Bardstown RD - Onsite Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Three bedroom (2 queen and 1 full), three bath house with complete eat-in kitchen, separate dinning room and formal livi ...
From $250 per night (USD)VRBO
- From $212 per night (USD)
VRBO
Derby City Delight | LUX home in Perfect Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Step into a world where historic charm and modern elegance converge at Derby City Delight, your luxurious Louis ...
From $212 per night (USD)VRBO
- From $818 per night (USD)
Expedia
New! Legends Louisville - Highlands - 6bd\/3.5ba!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Alright! Alright! Alright! Welcome to Legends a throw back to some of the greatest musicians! A perfect spot on ...
From $818 per night (USD)Expedia
- From $92 per night (USD)
VRBO
Walk to Everything! Bourbon Trail & Cherokee Golf Course \n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The best Bardstown Road has to offer! It is an extremely walkable and bike-friendly neighborhood with countless local es ...
From $92 per night (USD)VRBO
- From $1395 per night (USD)
Expedia
Untouchable ~ 6BR 4BA Prohibition Era w\/Sky Deck
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Immerse yourself in the allure of prohibition-era elegance and relive the untouchable legacy of America's most infamous ...
From $1395 per night (USD)Expedia