Cherokee Park 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 $9429 per night (USD)
Expedia
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 $9429 per night (USD)Expedia
- From $488 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 $488 per night (USD)VRBO
- From $111 per night (USD)
Expedia
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 $111 per night (USD)Expedia
- From $104 per night (USD)
VRBO
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 $104 per night (USD)VRBO
- From $396 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 $396 per night (USD)Expedia
- From $116 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 $116 per night (USD)VRBO
- 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
- From $171 per night (USD)
VRBO
Elegant Home Steps to Restaurant Row!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The house is a beautiful two-bedroom, one bathroom home that sleeps up to six (6) people. The master bedroom has a brand ...
From $171 per night (USD)VRBO
- From $159 per night (USD)
Expedia
Private Bungalow with EV 2 Charger in 2 car garage, sleeps 6 private
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience a warm welcome just minutes from downtown! Our cozy retreat is ideally situated near the renowned Distillerie ...
From $159 per night (USD)Expedia
- From $906 per night (USD)
VRBO
Bonnycastle Blue~Lux 6BR Epic Backyard + Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
BNB Louisville welcomes you to "Bonnycastle Blue." A prime stay and play destination for your large group. Located in th ...
From $906 per night (USD)VRBO
- From $145 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 $145 per night (USD)Expedia
- From $319 per night (USD)
VRBO
Hip 3BR\/2BA Highlands Loft on BEST Part of Bardstown Road. Comfy & Convenient!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautifully updated loft with deck in Louisville's most popular location: the Heart of the Highlands on Bardstown Road. ...
From $319 per night (USD)VRBO
- From $791 per night (USD)
Expedia
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 $791 per night (USD)Expedia
- From $2338 per night (USD)
VRBO
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 $2338 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 $32 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 $32 per night (USD)VRBO
- From $377 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 $377 per night (USD)VRBO
- From $158 per night (USD)
VRBO
2BR -HISTORIC & BRIGHT *PERFECT SPOT-FRANKFORT AVE
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Summary: Walk to almost anything you need, restaurants, coffee shops, bookstores & boutique shops! Located in the trendy ...
From $158 per night (USD)VRBO
- From $248 per night (USD)
Expedia
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 $248 per night (USD)Expedia
- From $389 per night (USD)
VRBO
EPIC STOCKED BARDSTOWN RD 2B2BA HOME WITH INDOOR FIRE TABLE AND 3 PATIOS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Discover the lively spirit of Louisville's Highlands neighborhood! Nestled on Bardstown Rd, this 2BR2BA two story stand- ...
From $389 per night (USD)VRBO
- 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 $1409 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 $1409 per night (USD)VRBO
- From $360 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 $360 per night (USD)Expedia
- From $710 per night (USD)
VRBO
The Masters * Historic 6BR 5BA Highlands w\/FirePit
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
The Masters, BNB Louisville's historic beauty boasting 6 huge bedrooms includes 3 Primary Suites in a rare combination o ...
From $710 per night (USD)VRBO
- From $376 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 $376 per night (USD)Expedia
- From $838 per night (USD)
VRBO
Swanky & Upbeat Suites @ Bungalou + Bourbon Bar
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $838 per night (USD)VRBO
- From $2522 per night (USD)
VRBO
Bungalou \"Ultimate SILVER\" (Sleeps 31)
- Bedrooms:
- 11
- Bathrooms:
- 13
- Sleeps:
- 31
Summary: Sleeps up to 31!!! Bungalou's famous “Ultimate Privacy” SILVER Package awaits you at Louisville’s Premier “Stay ...
From $2522 per night (USD)VRBO
- From $508 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 $508 per night (USD)VRBO
- From $205 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 $205 per night (USD)Expedia
- From $897 per night (USD)
VRBO
Rooftop & Pub Suites @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 13
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $897 per night (USD)VRBO
- From $1374 per night (USD)
Expedia
Rooftop w\/ 4 Suites @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 17
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $1374 per night (USD)Expedia
- From $423 per night (USD)
VRBO
Swanky Suite @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $423 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Bourbon Pub @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $292 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $437 per night (USD)
VRBO
Upbeat Suite @ Bungalou + Bourbon Bar + Gameyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to Louisville’s Premier “Stay-n-Play” Destination at BUNGALOU!! Come experience this STUNNING Urban Oas ...
From $437 per night (USD)VRBO
- From $422 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 $422 per night (USD)VRBO
- From $238 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 $238 per night (USD)Expedia
- From $221 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 $221 per night (USD)VRBO
- From $2355 per night (USD)
Expedia
Highlands Gem w\/ hot tub, fire pit - walkable to Bardstown Rd
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Planning your Kentucky Derby trip? Hitting the Bourbon Trail? Planning some college visits? This gorgeous home will be a ...
From $2355 per night (USD)Expedia
- 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
- From $743 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 $743 per night (USD)VRBO
- From $317 per night (USD)
VRBO
Louisville Home w\/ Hot Tub in The Highlands!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 6
Nestled in the heart of the bustling Highlands neighborhood, this 3-bedroom, 2-bathroom house is the perfect destination ...
From $317 per night (USD)VRBO
- From $855 per night (USD)
Expedia
Highlands Derby City Dream ~ 6BR+Hot Tub Sleep 14
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
The ALL NEW "Highlands Derby City Dream" by BNB Louisville is a premier destination located in the heart of Louisville's ...
From $855 per night (USD)Expedia
- From $87 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 $87 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
- Click For Pricing
VRBO
Highland Station at The Bellwether Hotel
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: With a nod to 1940’s design, this four bedroom and two bath space is perfect for larger groups. The fully equip ...
Click For PricingVRBO
- Click For Pricing
Expedia
Mossrose Suite 203 at The Bellwether Hotel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Immerse yourself in the era of Art Deco design when you settle into our Mossrose Suite. Working with the exist ...
Click For PricingExpedia
- Click For Pricing
VRBO
Henry Suite 207 at The Bellwether Hotel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Immerse yourself in the era of Art Deco design when you settle into our Henry Suite. Working with the existing ...
Click For PricingVRBO
- Click For Pricing
Expedia
Tyler Suite 209 at The Bellwether Hotel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Immerse yourself in the era of Art Deco design when you settle into our Everett Suite. Working with the existi ...
Click For PricingExpedia
- Click For Pricing
VRBO
Glenmary Suite 204 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 Suite. Working with the existing archi ...
Click For PricingVRBO
- Click For Pricing
Expedia
Rosewood Suite 202 at The Bellwether Hotel
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summary: Immerse yourself in the era of Art Deco design when you settle into our Rosewood Suite. Working with the exist ...
Click For PricingExpedia
- From $4368 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 $4368 per night (USD)VRBO
- From $75 per night (USD)
Expedia
2BR - FRANKFORT AVE - WALK & DINE - *BEST SPOT!!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $75 per night (USD)Expedia
- 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 $363 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 $363 per night (USD)VRBO
- From $561 per night (USD)
VRBO
\"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 $561 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 $202 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 $202 per night (USD)VRBO
- From $1544 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 $1544 per night (USD)Expedia
- From $132 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 $132 per night (USD)VRBO
- From $978 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 $978 per night (USD)VRBO
- From $88 per night (USD)
VRBO
Location, Location - 2BR\/1BA-Steps from Frankfort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly refurbished home located within walking distance of Frankfort Ave. 10 minutes to University of Louisville, Downto ...
From $88 per night (USD)VRBO
- From $535 per night (USD)
Expedia
Highlands Bungalow - Close to All
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 12
Summary: ( Beautiful century old charming bungalow house (3,300sq), centrally located - close to EVERYTHING!) The Highl ...
From $535 per night (USD)Expedia
- From $220 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 $220 per night (USD)VRBO
- From $686 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 $686 per night (USD)Expedia
- From $1145 per night (USD)
VRBO
All modern amenities, Huge deck, Fire Pit and Hot Tub, Walk to Dine and Fun!
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 14
Stunning 6000 square foot Italianate mansion in Louisville's National Preservation District with additional 1800 square ...
From $1145 per night (USD)VRBO
- From $175 per night (USD)
Expedia
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)Expedia
- From $755 per night (USD)
VRBO
Lux Highlands Spectacular with Sky Deck ~ 6BR 4BA
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Spectacular Spectacular! BNB Louisville welcomes you to this breathtaking BEAUTY in the heart of the Highlands, ready to ...
From $755 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $159 per night (USD)
VRBO
☼ 2 Bedrooms New \/ Elegant \/ Calm in HIP Highlands ► Walkable
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Ideally located Carriage House in the Highlands - Cherokee Triangle – 2 Beds (1 queen, 2 twins) / 1 bath (Partitioned fo ...
From $159 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Modern Louisville Apartment w\/ Furnished Deck
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $223 per night (USD)Expedia
- From $412 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 $412 per night (USD)VRBO
- From $62 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 $62 per night (USD)VRBO
- From $332 per night (USD)
VRBO
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 ...
From $332 per night (USD)VRBO
- 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
- From $221 per night (USD)
VRBO
Historic District Townhouse in City's BEST Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A perfectly located, modern town home located in the Cherokee Triangle Historic Preservation District. Less than 500 fee ...
From $221 per night (USD)VRBO
- From $337 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 $337 per night (USD)Expedia
- Click For Pricing
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
- 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
- From $237 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 $237 per night (USD)VRBO
- From $814 per night (USD)
Expedia
The Bonnycastle Massive 6BR New Orleans Themed Speakeasy with Bourbon Game Room
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
With 8 beds (2 Kings, 4 Queens, 1 Full, 1 Twin) we have room for 15 guests. Experience our historic 6BR, 3BA Louisville ...
From $814 per night (USD)Expedia
- From $132 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 $132 per night (USD)VRBO
- From $196 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 $196 per night (USD)Expedia
- From $658 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 $658 per night (USD)VRBO
- From $1239 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 $1239 per night (USD)VRBO
- From $73 per night (USD)
VRBO
The Pegasus Luxury and Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
The Pegasus reflects the soul of the City. Come experience the hum of excitement that permeates Louisville in the days l ...
From $73 per night (USD)VRBO
- From $234 per night (USD)
Expedia
Cottage Park Carriage House. Rest & Explore with Hollyhock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
See all suites & promotions at www.hollyhocksuites This apartment is located in the carriage house of a historic mansio ...
From $234 per night (USD)Expedia
- From $162 per night (USD)
VRBO
Location & Luxury - Welcome to your private suite!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private suite with smart lock entrance in the best location Louisville has to offer. Located one street away from Bardst ...
From $162 per night (USD)VRBO
- 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
- From $1324 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 $1324 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $1113 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 $1113 per night (USD)VRBO
- From $528 per night (USD)
Expedia
Renovated Historic Home, Walk to All! 4 bedrooms\/baths, large deck and grill
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
24 hour self check in available! Details below. A well appointed, comfortable home in a fantastic location. Walk to d ...
From $528 per night (USD)Expedia
- From $980 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 $980 per night (USD)VRBO
- From $713 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 $713 per night (USD)Expedia
- From $92 per night (USD)
VRBO
The Secretariat * Highlands * Derby * Pet Friendly* Restaurant Row*Cherokee Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
The Secretariat reflects the soul of the City. Come experience the hum of excitement that permeates Louisville in the da ...
From $92 per night (USD)VRBO
- From $1818 per night (USD)
VRBO
Highlands Oasis with Swimming Pool and Gourmet Kitchen
- Bedrooms:
- 4
- Bathrooms:
- 6
- 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 $1818 per night (USD)VRBO
- From $65 per night (USD)
VRBO
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 $65 per night (USD)VRBO
- From $593 per night (USD)
Expedia
Walk to Dinner, Pubs, Fun- Huge Historic District Home with Poker Room, Fire Pit
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
NOTE: Kentucky Derby 2025 weekend bookings must be pre-cleared. Please message prior to booking. Easy, 24 hour check ...
From $593 per night (USD)Expedia