Cherokee Park Rentals
- From $6415 per night (USD)
VRBO
Luxurious Retreat KY Derby & PGA - Exquisite Reno
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Willow Avenue, your exclusive haven in the heart of Louisville's Highlands, offering an unparalleled experien ...
From $6415 per night (USD)VRBO
- From $799 per night (USD)
Expedia
Louisville KY Historical Mansion! *Bourbon Trail*
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to a breathtaking circa 1923 fully renovated colonial home where rich magical history meets modern amenities. Lo ...
From $799 per night (USD)Expedia
- From $125 per night (USD)
VRBO
Clifton Two Bedroom House!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Entire single family home. You will be close to everything when you stay at this centrally-located house. Walking distan ...
From $125 per night (USD)VRBO
- From $93 per night (USD)
Expedia
Condo in the Highlands walkable to restaurants, bars, and shopping
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is in the heart of the popular Highlands neighborhood. Steps away from restaurants, bars, and shops on Baxte ...
From $93 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Regal Mansion w Private Garden in Quiet Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Elegant Louisville Suite with Lush Garden, Ideal for City and Nature Lovers. The Space: Step into the tranquil ...
From $278 per night (USD)VRBO
- From $89 per night (USD)
Expedia
Cozy Retreat Near Expo Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Step into the nostalgic embrace of "Highland Haven," a serene Louisville gem in a historic, walkable neighborho ...
From $89 per night (USD)Expedia
- From $249 per night (USD)
VRBO
Bed & Bourbon, Classic, Walk, Close to Everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: - Award Winning Accommodations - The Bourbon Review - Bourbon Themed House - Perfect for groups touring Bourbo ...
From $249 per night (USD)VRBO
- From $249 per night (USD)
Expedia
4 bedrooms in Highlands Bardstown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A beautiful refinished hardwood staircase built in 1910 greets you as you enter. This large duplex house has over 2000 s ...
From $249 per night (USD)Expedia
- From $249 per night (USD)
VRBO
Charming 1BR Retreat in the Heart of Louisville's Highlands
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 7
Welcome to your serene getaway nestled in the vibrant heart of Louisville's beloved Highlands neighborhood! This beautif ...
From $249 per night (USD)VRBO
- From $458 per night (USD)
Expedia
Derby and PGA rental in Cherokee Triangle in the heart of the Highlands!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful home in Cherokee Triangle with updated kitchen, large master suite, sleeps six. Three blocks from Bardstown Ro ...
From $458 per night (USD)Expedia
- From $93 per night (USD)
VRBO
Highlands Apartment Close to Downtown, Local shops\/restaurants\/bars\/park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Brand new 2 bedroom apartment in the heart of the Highlands. Within 2 miles of several major hospitals and the downtown ...
From $93 per night (USD)VRBO
- From $950 per night (USD)
Expedia
\"The Inn Field\" Louisville, KY Derby Home near Bardstown Road in the Highlands
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
In the heart of the Highlands, you will find that “The Inn Field” is a stylish home nestled on a street filled with char ...
From $950 per night (USD)Expedia
- From $872 per night (USD)
VRBO
Historic haven ready for 150th KY Derby and PGA
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to your historic retreat in the heart of Highlands, Kentucky! This magnificent three-story house, steeped in ric ...
From $872 per night (USD)VRBO
- From $2500 per night (USD)
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 ...
From $2500 per night (USD)Expedia
- From $804 per night (USD)
VRBO
Kentucky Derby, PGA & Bourbon Trail \nLousiville Historic Home
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
A charming home with stylish interiors located on Frederick Law Olmsted’s idyllic Cherokee Park. Features a tremendous m ...
From $804 per night (USD)VRBO
- From $216 per night (USD)
Expedia
Buddha's Bungalow above the Highlands
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
In the Heart of the Highlands, Louisville's premier entertainment district, with world class restaurants and eclectic sh ...
From $216 per night (USD)Expedia
- Click For Pricing
VRBO
Trendy Condo walking Distance to Bars, Restaurants, and Coffee Shop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Single Barrel Retreat has an unbeatable location! This stylish upstairs condo is designed with KY in mined (subtle horse ...
Click For PricingVRBO
- From $437 per night (USD)
Expedia
Spacious Louisville Home: Walk to Restaurants!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover the best of the Bluegrass State from this ideally located 4-bedroom, 2-bathroom vacation rental, situated just ...
From $437 per night (USD)Expedia
- From $8100 per night (USD)
VRBO
Historic, Luxury House in Prime Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
End-to-end one of the best houses in Louisville in a prime location ! Relax and enjoy this luxury house offering ultra- ...
From $8100 per night (USD)VRBO
- From $111 per night (USD)
Expedia
Walkable! Cozy! Summ
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to the Thoroughbred Retreat! This is the premier couple's or solo traveler guest suite in Louisville! T ...
From $111 per night (USD)Expedia
- From $139 per night (USD)
VRBO
The Bourbon King - Walk to everything! Cozy! Chic!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to the Bourbon King! This is the premier couple's or solo traveler guest suite in Louisville! This exce ...
From $139 per night (USD)VRBO
- From $117 per night (USD)
Expedia
Local Legends Lounge - Walkable to fun- Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to the Local Legends Lounge! This is the premier couple's or solo traveler guest suite in Louisville! T ...
From $117 per night (USD)Expedia
- From $134 per night (USD)
VRBO
Private Bungalow with EV 2 Charger in 2 car garage, sleeps 6 private
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a warm welcome just minutes from downtown! Our cozy retreat is ideally situated near the renowned Distillerie ...
From $134 per night (USD)VRBO
- From $106 per night (USD)
Expedia
Luxe 2BR Home on Famous St.\/Sleeps 5\/Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
• Easy access remodeled apartment • Situated on the most famous street in Louisville • Sleeps 5 in 2 queen beds and slee ...
From $106 per night (USD)Expedia
- From $161 per night (USD)
VRBO
Highlands Three Bedroom House - Walk to Restaurants and Bars!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious three bedroom house with dining room and fully stocked kitchen. First floor master with ensuite, and two addit ...
From $161 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $492 per night (USD)
VRBO
Charming HOTTUB oasis! SLEEPS 12 & FREE parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
House has been partially updated with fresh new modern look AND A HOT TUB!! Free Private parking in back of property, p ...
From $492 per night (USD)VRBO
- From $274 per night (USD)
Expedia
King Bed, walk to restaurants, shops, and nightlife. Private Fenced Backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience our historic 2BR, 2BA Louisville Highland duplex, echoing of an old New Orleans speakeasy, nestled in a tranq ...
From $274 per night (USD)Expedia
- From $621 per night (USD)
VRBO
The Masters * Historic 6BR 5BA Highlands w\/FirePit
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
The Masters, BNB Louisville's historic beauty boasting 6 huge bedrooms includes 3 Primary Suites in a rare combination o ...
From $621 per night (USD)VRBO
- From $115 per night (USD)
Expedia
Taste of KY Studio @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $115 per night (USD)Expedia
- From $844 per night (USD)
VRBO
Rooftop & Pub Suites @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 13
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $844 per night (USD)VRBO
- From $1340 per night (USD)
Expedia
Rooftop w\/ 4 Suites @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 17
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $1340 per night (USD)Expedia
- From $548 per night (USD)
VRBO
6BR\/3BA PRIME Location - Entire Home (Both Units)
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
NEWLY RENOVATED duplex is perfect for groups! Upstairs unit is 3BR/1BA and the first floor unit is 3BR/2BA. Your group w ...
From $548 per night (USD)VRBO
- From $314 per night (USD)
Expedia
Excellent 3BR\/2BA PRIME Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
NEWLY RENOVATED 3 Bed 2 Bath lower level of duplex is perfect for small groups, couples, or business travelers. Upon arr ...
From $314 per night (USD)Expedia
- From $85 per night (USD)
VRBO
Bright, Parkside condo with pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**MINIMUM OF 30 DAY RENTALS.** This 2,200 sq foot, first floor condo is fully furnished with two bedrooms, kitchen, bat ...
From $85 per night (USD)VRBO
- Click For Pricing
Expedia
LouLounge Studio @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
Click For PricingExpedia
- From $2557 per night (USD)
VRBO
Historic Peterson Mansion
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 15
Welcome to Historic Crescent Hill and Frankfort avenue. This 1900 Home is situated next door to a historic house & park ...
From $2557 per night (USD)VRBO
- From $55 per night (USD)
Expedia
Highland Victorian Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 31
The apartment is located half a block from some of the best restaurants in Louisville. On the other end of the street is ...
From $55 per night (USD)Expedia
- From $67 per night (USD)
VRBO
2BR - FRANKFORT AVE - WALK & DINE - *BEST SPOT!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Loft in the heart of trendy the Clifton/Frankfort Ave corridor. This unit has been designed with a fun mix ...
From $67 per night (USD)VRBO
- From $1300 per night (USD)
Expedia
Parklike Estate in the Heart of Louisville w\/Pool and Gardens -- Family Friendly
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
PLEASE READ: We love to know why our guests are coming to Louisville -- please tell us a little bit about your group whe ...
From $1300 per night (USD)Expedia
- From $101 per night (USD)
VRBO
Stylish Loft in Vibrant Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
NEWLY RENOVATED 2 Bed 1 Bath loft is perfect for small groups, couples, or business travelers. Upon arrival you'll be gr ...
From $101 per night (USD)VRBO
- From $455 per night (USD)
Expedia
Highlands Bungalow - Close to All
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
Summary: ( Beautiful century old charming bungalow house (3,300sq), centrally located - close to EVERYTHING!) The Highl ...
From $455 per night (USD)Expedia
- From $192 per night (USD)
VRBO
Louisville's Best Area, Walk to All!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Our townhouse has 24 hour digital check in! See details below. This perfectly located townhouse is in Louisville's prem ...
From $192 per night (USD)VRBO
- From $908 per night (USD)
Expedia
The Big Chill-New Hot Tub! MEGA DECK! Walk to Fun!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Are you looking for a premier vacation home when visiting Louisville? Stop looking, you've found it! Premier ...
From $908 per night (USD)Expedia
- From $995 per night (USD)
VRBO
All modern amenities, Huge deck, Fire Pit and Hot Tub, Walk to Dine and Fun!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Stunning 6000 square foot Italianate mansion in Louisville's National Preservation District with additional 1800 square ...
From $995 per night (USD)VRBO
- From $375 per night (USD)
Expedia
\"Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!\"
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
"Welcome to Highlands Lookout: A Modern Retreat for Your Louisville Adventure! Step into contemporary comfort on Bardst ...
From $375 per night (USD)Expedia
- From $899 per night (USD)
VRBO
Bourbon Mansion 3 Story Walk to Restaurants Park
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
*Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required ...
From $899 per night (USD)VRBO
- Click For Pricing
Expedia
STUNNING HIGHLANDS 5 BED NIGHT AT THE MUSEUM
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious five bedroom house in the middle of The Highlands. Perfect for large groups. Walk to restaurants, bars and ot ...
Click For PricingExpedia
- From $155 per night (USD)
VRBO
Historic District Townhouse in City's BEST Location
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
A perfectly located, modern town home located in the Cherokee Triangle Historic Preservation District. Less than 500 fee ...
From $155 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Close To Downtown In Historic Crecent Hill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Large, well maintained home in a quiet neighborhood minutes from interstates 71, 64 and 65 and downtown. Within walking ...
From $175 per night (USD)Expedia
- From $130 per night (USD)
VRBO
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located in safe & quiet Crescent Hill within walking distance to restaurants, shopping, parks & more. 2 bed 1 bath with ...
From $130 per night (USD)VRBO
- From $690 per night (USD)
Expedia
The Bonnycastle Massive 6BR New Orleans Themed Speakeasy with Bourbon Game Room
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
Experience our historic 6BR, 3BA Louisville Highland home, echoing of an old New Orleans speakeasy, nestled in a tranqui ...
From $690 per night (USD)Expedia
- Click For Pricing
Expedia
Highlands Charming Nightlife Oasis!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
UPDATE *9/8/2021*: This apartment has been partially remodeled due to recent issues! New floors and some new furnishings ...
Click For PricingExpedia
- From $105 per night (USD)
VRBO
Highlands Zen Oasis Cherokee Parkside-KING Suite, Plush, Private, UltraCozy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Here? You are locked & stocked. Home sweet insta-home. This newly updated PRIVATE APT. has almost everything you could n ...
From $105 per night (USD)VRBO
- From $68 per night (USD)
VRBO
The Pegasus Luxury and Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Pegasus reflects the soul of the City. Come experience the hum of excitement that permeates Louisville in the days l ...
From $68 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Park Carriage House. Rest & Explore with Hollyhock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
This apartment is located in the carriage house of a historic mansion in beautiful Crescent Hill. Location is one block ...
From $144 per night (USD)Expedia
- From $127 per night (USD)
VRBO
Location & Luxury - Welcome to your private suite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private suite with smart lock entrance in the best location Louisville has to offer. Located one street away from Bardst ...
From $127 per night (USD)VRBO
- From $101 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 $101 per night (USD)Expedia
- From $1084 per night (USD)
VRBO
The Mint Julep, huge 7 bedroom house in heart of the Highlands
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 24
This large brand new home is available for your family or group of friends. Remodeled from top to bottom. Home feature ...
From $1084 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Renovated Historic Home, Walk to All! 4 bedrooms\/baths, large deck and grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
24 hour self check in available! Details below. A well appointed, comfortable home in a fantastic location. Walk to d ...
From $338 per night (USD)Expedia
- From $810 per night (USD)
VRBO
The Louis on Longest - Prime Louisville Location! In the heart of the Highlands.
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 18
Louis on Longest is located in the heart of The Highlands just off Bardstown Road. This newly renovated home offers mult ...
From $810 per night (USD)VRBO
- From $314 per night (USD)
Expedia
Victorian Retreat ~ Historic Highlands 4 Bedroom
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
BNB Louisville presents: Victorian Retreat, a gorgeous mix of period details and modern finishes highlight this Victoria ...
From $314 per night (USD)Expedia
- From $87 per night (USD)
VRBO
The Secretariat * Highlands * Derby * Pet Friendly* Restaurant Row*Cherokee Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Secretariat reflects the soul of the City. Come experience the hum of excitement that permeates Louisville in the da ...
From $87 per night (USD)VRBO
- From $62 per night (USD)
Expedia
The Filly - 6 miles to Churchill Downs - Pets - Highlands\/Cherokee Triangle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Filly is a one bedroom basement unit that has been fully renovated into a nice bright comfortable spacious living ar ...
From $62 per night (USD)Expedia
- From $410 per night (USD)
VRBO
Walk to Dinner, Pubs, Fun- Huge Historic District Home with Poker Room, Fire Pit
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
NOTE: Kentucky Derby 2025 weekend bookings must be pre-cleared. Please message prior to booking. Easy, 24 hour check ...
From $410 per night (USD)VRBO
- Click For Pricing
Expedia
Stunning Kentucky Derby home located only 6 miles from the Track
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Situated on one of the city’s most beautiful streets, in one of the world’s most beautiful cities, this three bedroom ho ...
Click For PricingExpedia
- From $128 per night (USD)
VRBO
Beautiful - walkable - Cozy Highlands Studio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: If you want unique, walkable, and cozy - Here's your spot! Historic, mindful renovations, tons of natural ligh ...
From $128 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Kentucky Derby Churchill Downs 10 mins Amazing Area
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
The Frankfort Avenue Coach House! If you book via this website please be aware that the price here is for guest stay onl ...
From $595 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Highlands Oasis with Swimming Pool and Gourmet Kitchen
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Look no further, the highlands oasis has everything you need to make your visit perfect! With a large chef's kitchen, a ...
From $1500 per night (USD)VRBO
- From $60 per night (USD)
VRBO
Rental of cabs in the highlands
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 950 sq foot, loft-style carriage house, with 17 foot ceilings, is fully furnished with kitchen, bath, washer/dryer, ...
From $60 per night (USD)VRBO
- From $1064 per night (USD)
VRBO
High Above Highlands large 6 bedroom home in fantastic urban area!
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 18
Welcome to HIGH ABOVE THE HIGHLANDS!!! This place is in a word: AMAZING!!! 3 floors, designer decorated, 6 bedrooms, 3.5 ...
From $1064 per night (USD)VRBO
- From $921 per night (USD)
VRBO
Heart Of the Highlands Hangout-Large 7 Bedroom!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 24
This large brand new home is available for your family or group of friends. Remodeled from top to bottom. Home feature ...
From $921 per night (USD)VRBO
- Click For Pricing
VRBO
Centrally Located Home for Derby\/Breeders Cup
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Recently renovated home in the Highlands close to airport, Churchill Downs and downtown. The best restaurants, bars and ...
Click For PricingVRBO
- From $382 per night (USD)
VRBO
PAYNE ST PADDOCK, crescent hill, highlands, NULU, st. matthews
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Frankfort Ave. corridor, or what locals call "The Avenue" Walk to restaurants and shops! Relax at your re ...
From $382 per night (USD)VRBO
- From $2286 per night (USD)
VRBO
Remodeled Designer Home Near Restaurants, Parks & Track
- Bedrooms:
- 4
- 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 $2286 per night (USD)VRBO
- From $114 per night (USD)
VRBO
☼ 2 Bedrooms New \/ Elegant \/ Calm in HIP Highlands ► Walkable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ideally located Carriage House in the Highlands - Cherokee Triangle – 2 Beds (1 queen, 2 twins) / 1 bath (Partitioned fo ...
From $114 per night (USD)VRBO
- From $252 per night (USD)
VRBO
The Highlands Happy Place!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Look no further, You have found your happy place! James Wallace & Co.'s latest offering! This apt. home is located on ...
From $252 per night (USD)VRBO
- From $923 per night (USD)
VRBO
Lux Highlands Spectacular with Sky Deck ~ 6BR 4BA
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Spectacular Spectacular! BNB Louisville welcomes you to this breathtaking BEAUTY in the heart of the Highlands, ready to ...
From $923 per night (USD)VRBO
- From $821 per night (USD)
VRBO
Kentucky Derby - Ideal Bardstown Rd area Close Restaurnts\/Bars
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Tremendous house in the Heart of Cherokee Triangle. Prime location within walking distance to Bardstown Road. Available ...
From $821 per night (USD)VRBO
- From $1133 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 $1133 per night (USD)VRBO
- From $323 per night (USD)
VRBO
Cozy Bardstown Rd Apartment | W\/D, Fast Wifi, Porch, Parking, Location!! ❤️
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Whether you're sampling local cuisine, discovering unique boutiques, or simply soaking in the vibrant atmosphere, this d ...
From $323 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Upbeat Suite @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $463 per night (USD)VRBO
- From $553 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 $553 per night (USD)VRBO
- From $995 per night (USD)
VRBO
Bourbon Lovers and Bardstown Road - Epic Sky Deck - Sleeps 14+
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to the Bardstown! This kick-ass house has six bedrooms nine beds and three and half baths. We love love love b ...
From $995 per night (USD)VRBO
- From $211 per night (USD)
VRBO
3BR\/1.5BA Home w\/ Relaxing HOT TUB in Popular Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make memories in 'The Gateway to the South' when you book this 3-bedroom, 1.5-bathroom house! Featuring over 1,600 squar ...
From $211 per night (USD)VRBO
- From $444 per night (USD)
Expedia
Swanky Suite @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $444 per night (USD)Expedia
- From $283 per night (USD)
VRBO
Bourbon Pub @ 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 $283 per night (USD)VRBO
- From $423 per night (USD)
Expedia
4BR, 1-King, Gourmet Kitchen , Derby NULU EXPO, walk to shops, dining, nightlife
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
This historic Louisville home is rich in character while offering modern conveniences. The spacious home is nestled in a ...
From $423 per night (USD)Expedia
- From $825 per night (USD)
VRBO
Swanky & Upbeat Suites @ Bungalou + Bourbon Bar
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $825 per night (USD)VRBO
- From $2338 per night (USD)
VRBO
Bungalou \"Ultimate SILVER\" (Sleeps 31)
- Bedrooms:
- 11
- Bathrooms:
- 10
- Sleeps:
- 31
Summary: Sleeps up to 31!!! Bungalou's famous “Ultimate Privacy” SILVER Package awaits you at Louisville’s Premier “Stay ...
From $2338 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Rooftop Suite @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $339 per night (USD)VRBO
- From $731 per night (USD)
VRBO
Perfect Derby or PGA Home, Charming Highlands Rental
- 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 $731 per night (USD)VRBO
- From $1214 per night (USD)
VRBO
Make this your home base for the Kentucky Derby!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our recently remodeled ranch in the city is close to everything. We have 3 bedrooms and 3 baths perfect for 6 guests, ea ...
From $1214 per night (USD)VRBO
- From $298 per night (USD)
VRBO
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
*** We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning ...
From $298 per night (USD)VRBO
- From $30 per night (USD)
VRBO
Cozy Oasis In The Highlands with Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unit is in the basement of a duplex with kitchen, incl. a convection/microwave, sink, under-counter refrigerator. Bed no ...
From $30 per night (USD)VRBO
- From $536 per night (USD)
VRBO
Charming 3-BR \/ 2-BR home in Derby City! Close to everything Louisville offers!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home...a beautiful 97-year old treasure in the heart of the Highlands neighborhood. Minut ...
From $536 per night (USD)VRBO
- From $775 per night (USD)
VRBO
The Highlands Hangout, EXPO, DOWNTOWN, restaurant row!!! Game room & LOCATION!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
*** We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning ...
From $775 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Hot tub, Highlands-Restaurant Row Churchill Downs, Zoo, Bellarmine, Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Louisville's Restaurant Row & The Southern Comfort Family Retreat - a well-appointed 4 bedroom (7 beds), 2 ...
From $460 per night (USD)Expedia
- From $90 per night (USD)
VRBO
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 $90 per night (USD)VRBO
- From $100 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 $100 per night (USD)VRBO