Cherokee Park, Kentucky Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Cherokee Park, Kentucky on RentalSaver.com!

Cherokee Park Rentals

From $325 per night (USD)
VRBO
Entire Home in the Highlands on Bardstown RD - Onsite Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy your stay in one of the city's best locations. This three-bedroom (2 queens and 1 full), three-bath house is locat ...
From $325 per night (USD)
VRBO
From $512 per night (USD)
Expedia
Derby City Delight | LUX home in Perfect Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Step into a world where historic charm and modern elegance converge at Derby City Delight, your luxurious Louis ...
From $512 per night (USD)
Expedia
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VRBO
Kentucky Derby or PGA Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Best Location -9 miles from Churchill Downs Located in Louisville's most sought after neighborhood Located in the Heart ...
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VRBO
From $2694 per night (USD)
Expedia
Derby City's Finest - Luxury Home in the heart of historic Crescent Hill
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Located in Louisville's charming Crescent Hill neighborhood, this fully renovated historic home has it all! Situated in ...
From $2694 per night (USD)
Expedia
From $631 per night (USD)
VRBO
Charming Highlands Duplex: Historic Elegance, Modern Comfort
Bedrooms:
2
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 $631 per night (USD)
VRBO
From $641 per night (USD)
Expedia
The Cherokee Homestead/ 5BR home/ Great location!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Are you planning a family or friends' getaway? Look no further! Our beautiful, comfortable, and spacious home is the ide ...
From $641 per night (USD)
Expedia
From $874 per night (USD)
VRBO
Untouchable~6BR 4BA Speakeasy w/Sky Deck+Fire Pit
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
BNB Louisville introduces the ULTIMATE way to experience the Bourbon Trail through the allure of Prohibition-era eleganc ...
From $874 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Highlands Bourbon Retreat ~ 4BR 3BA
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
BNB Louisville welcomes you to this breathtaking BOURBON RETREAT in the heart of the Highlands. It's the absolute PRIME ...
From $481 per night (USD)
Expedia
From $377 per night (USD)
VRBO
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 $377 per night (USD)
VRBO
$Walk to Everything! Bourbon Trail & Cherokee Golf Course \n$
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Expedia
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 ...
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Expedia
From $171 per night (USD)
VRBO
Steps to Restaurants, Nightlife, Shops~PacMan/King Bed~Bardstown Rd/Highlands
Bedrooms:
1
Bathrooms:
2
Sleeps:
9
**NEW VRBO PRICING STRUCTURE: Effective June 2025 VRBO displays all-in pricing on the main listing page which includes t ...
From $171 per night (USD)
VRBO
From $435 per night (USD)
VRBO
Large 4-bdrm historic Highlands home just steps to bars, parks and restaurants!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
NEW LISTING!! Just minutes from airport and downtown with easy Uber access. Discover the beauty of Louisville for a week ...
From $435 per night (USD)
VRBO
From $276 per night (USD)
VRBO
Cozy Casa Perfect Family Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This stunning fully furnished home is the perfect blend of modern luxury and comfort. Located in a beautiful neighborhoo ...
From $276 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Big Chill! 5br 2ba Walkable- Hot tub!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Looking for a beautiful homebase for your stay in Louisville? Stop looking, you've found it! Premier walkable ...
From $538 per night (USD)
Expedia
From $924 per night (USD)
VRBO
Highlands 8 Bedroom 3B Bath w/13 Beds Sleep 18! + Fire Pit Pool Table
Bedrooms:
3
Bathrooms:
8
Sleeps:
16
Introducing Baxter Manor, BNB Louisville's stunning property located at 965 Baxter Ave in Louisville. This beautiful hom ...
From $924 per night (USD)
VRBO
From $580 per night (USD)
Expedia
The Reserve~Stunning 5BR 4BA w/HotTub
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
**BRAND NEW** You've just discovered the pinnacle of modern luxury wrapped in a bourbon-soaked vibe that’s totally on po ...
From $580 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Home In The Highlands! 5br/2ba Walkable! Hot tub!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Exciting home with plenty of space in Louisville's most walkable neighborhood! Walk to fun and entertainment, ...
From $521 per night (USD)
VRBO
From $525 per night (USD)
Expedia
The Mash Lou– Walk to Frankfort Ave Dining & Nightlife -Near Downtown Louisville
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Louisville adventure days, Frankfort Avenue nights! Soak in the electric spirit of Louisville (bourbon tour perhaps?) by ...
From $525 per night (USD)
Expedia
From $674 per night (USD)
VRBO
KY DERBY @The Cherokee Charmer! ….5 Miles from Churchill Downs !!!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Historic Home located blocks from the "Highlands" of Louisville KY where you will find the most exquisite dining, the b ...
From $674 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Classic Heart of Highlands! 3BR!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to your serene retreat in an unbeatable location! This beautifully designed and fully renovated 3-bedroom, 1-bat ...
From $150 per night (USD)
Expedia
From $107 per night (USD)
VRBO
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 $107 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Contemporary Stay in Louisville's Vibrant Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Discover Louisville’s vibrant Highlands neighborhood from this centrally located retreat, steps from eclectic s ...
From $315 per night (USD)
Expedia
From $71 per night (USD)
VRBO
Charming, pet friendly studio in walkable Clifton, Louisville with full kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the popular, historic and very walkable Clifton Neighborhood, this adorable property is a comfortable, cozy, ...
From $71 per night (USD)
VRBO
From $270 per night (USD)
VRBO
New Custom & Creative Louisville Carriage House: expansive deck, wifi, walkable
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our newly built Louisville Carriage House is thoughtfully designed for relaxation and productivity. Experience style, co ...
From $270 per night (USD)
VRBO
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VRBO
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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VRBO
From $791 per night (USD)
Expedia
NEW Historic Highlands Retreat! Prime Location Gem
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Summary: Located in the heart of the Highlands, this charming 100+ year-old home offers three separate living spaces, pe ...
From $791 per night (USD)
Expedia
From $326 per night (USD)
VRBO
NEW! Cozy Unit in the Heart of the Highlands!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Stay in the heart of Louisville’s Highlands at this charming 100+ year-old home, blending historic character wi ...
From $326 per night (USD)
VRBO
From $308 per night (USD)
Expedia
NEW! Cozy Historic Retreat| Heart of the Highlands
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Discover Louisville’s vibrant Highlands from this charming 100+ year-old home on Bardstown Rd. This updated 1-b ...
From $308 per night (USD)
Expedia
From $328 per night (USD)
VRBO
NEW Cozy Studio Unit in the Heart of the Highlands
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Discover your ideal Louisville stay in this charming Highlands studio unit on Bardstown Rd. Set in a 100+ year- ...
From $328 per night (USD)
VRBO
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 $193 per night (USD)
VRBO
Cozy Unit w/ Backyard Access | Near Bourbon Trail!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Explore Louisville’s vibrant Highlands from this bright 2-bedroom suite, perfect for families, friends, or busi ...
From $193 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Cozy Home | 1BR Near Downtown + Prime Location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Discover Louisville’s Bardstown Road in this spacious 1-bedroom suite, blending comfort with a vibrant, artisti ...
From $264 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Rebel Retreat | HotTub | 6 bedrm | Game Rm| Fire Pit | Jet Shwrs
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Welcome to Rebel Retreat—your unapologetically bold, bourbon-soaked basecamp in the heart of Louisville’s Highlands. Thi ...
From $642 per night (USD)
VRBO
Click For Pricing
Expedia
Highlands Hidden Gem 4BR apt w/ free parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Enjoy your afternoons exploring the Highlands in this spacious, 4 Bedroom 2 Full Bath hidden gem! The apartm ...
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Expedia
From $179 per night (USD)
VRBO
4BR/2BA Charming Louisville Getaway!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This spacious and welcoming 4-bedroom 2-bathroom home is perfect for families or groups, featuring a king bed, two queen ...
From $179 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Highlands Lookout-3BR 3.5BA-Walk to Tons +Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Highlands Lookout, your ultimate spot for a good time on Bardstown Road in the lively Highlands of Louisville ...
From $410 per night (USD)
Expedia
From $1195 per night (USD)
VRBO
Gatsby House | Luxe 3BR + Game Room Near Bardstown
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Step into The Gatsby House—a fully restored 1900s mansion where historic charm meets modern luxury. Located jus ...
From $1195 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
Chic 3BR Lou Speakeasy Unit | Perfect for Groups!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Experience Louisville in style- perfect for Derby, Bourbon & Beyond, or Forecastle weekends with friends. A spa ...
From $1168 per night (USD)
Expedia
$It's a Vibe in the Highlands.\nKing Bed & Queen bed$
From $212 per night (USD)
VRBO
It's a Vibe in the Highlands.\nKing Bed & Queen bed
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your artsy Highland haven in Louisville! Tucked away on a quiet, historic street on Rufer Avenue between Baxt ...
From $212 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Charming Studio Stay in Vibrant Highlands Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Located in the heart of the Highlands, this charming 100+ year-old home offers a cozy retreat. This studio unit ...
From $262 per night (USD)
Expedia
From $104 per night (USD)
VRBO
Cozy Studio in the Highlands, KY!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this stylish studio in the heart of Louisville! Thoughtfully designed for comfort, this cozy retreat features ...
From $104 per night (USD)
VRBO
From $597 per night (USD)
Expedia
H1: Bourbon &Derby Getaway+Gift
Bedrooms:
2
Bathrooms:
4
Sleeps:
18
Experience a refined vintage retreat in the heart of Louisville’s Highlands. Just steps from Bardstown Road’s renowned d ...
From $597 per night (USD)
Expedia
From $457 per night (USD)
VRBO
The Paddock ~ 5BR Class & Fun In One! Hot Tub, Fire Pit, Mini Golf, Walkable
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Feel right at home in this newly designed Louisville getaway! Class meets comfort with roomy spaces and king beds for al ...
From $457 per night (USD)
VRBO
From $663 per night (USD)
Expedia
The Stables ~ Hot Tub, Fire Pit & Games Steps From Bardstown Rd
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Your 6 bedroom Highlands retreat awaits—just ½ block from Louisville's historic Bardstown Rd! Enjoy roomy interiors with ...
From $663 per night (USD)
Expedia
From $373 per night (USD)
VRBO
The BAX I Spacious I Walkable I Patios
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in Louisville's vibrant Highlands neighborhood, this three-story retreat features two expansive outdoor patios w ...
From $373 per night (USD)
VRBO
From $469 per night (USD)
Expedia
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)
Expedia
From $226 per night (USD)
VRBO
Lovely 5BR Family-Friendly Home for a Relaxing Stay!
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
Bright, colorful, and spacious—this professionally decorated Louisville home is designed for comfort and fun! With room ...
From $226 per night (USD)
VRBO
From $140 per night (USD)
VRBO
Stylish 3BR Retreat in Kentucky
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Experience Vintage Charm with Modern Comforts in Louisville! Welcome to your stylish 3-bedroom retreat in the heart of ...
From $140 per night (USD)
VRBO
From $171 per night (USD)
VRBO
Cozy & Spacious 4BR Home in the Highlands!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy a spacious and inviting 4-bedroom home in Louisville—ideal for families, friends, or small groups. Each bedroom of ...
From $171 per night (USD)
VRBO

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Cherokee Park Rentals

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Results: 149 Rentals