Holiday rentals in Highlands

Bourbon Belle- Cozy Germantown home with parking!

Bourbon Bell- a newly renovated historic shotgun home in the heart of Germantown neighborhood. Welcome to this charming 2-BA, 1-BR cottage offering a comfy 832 sq ft of thoughtfully designed space. Ideal for a small group or couple, it features a plush queen bed, a fully equipped kitchen with modern appliances, & a cozy living area with a smart TV for streaming. Enjoy coffee on the porch or unwind in the private backyard after exploring Louisville’s nearby attractions, dining, & entertainment!

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Walk to everything • Quiet, Private, and Cozy

Tucked along a quiet, tree-lined street in Louisville’s Original Highlands neighborhood, you’ll find a cozy, private retreat filled with character and unique decor. Featuring a large master bedroom with king Sleep Number bed, a spacious living/dining room area, 2 full bathrooms, and a cozy full sized guest room. Walk to the best restaurants, boutiques, and coffee shops. Explore the nearby parks or unwind in your peaceful, historic hideaway. 1 mile from NULU 2 from downtown 5 from the Downs

Historic Hideaway w/Free Parking

Situated in the heart of a vibrant neighborhood, you'll find an array of exciting options for dining, drinks, coffee, and shopping right at your doorstep. With numerous restaurants serving diverse cuisines, trendy breweries offering craft beers, cozy coffee shops brewing aromatic blends, and chic boutiques showcasing local fashion and artisanal goods, you'll have plenty of choices to explore and indulge in the local scene. You'll be spoiled for choice with the plethora of options.

The Bardstown-Louisville Nightlife

This spacious unit provides a front row seat to watch and experience Louisville from the comfort of your own private retreat in the middle of the best street in Louisville. Feet from many restaurant , bars and boutiques. During your stay spend time walking the neighborhood filled with boutiques, restaurants, bars, distilleries and art galleries. Start the bourbon trail or walk to the famous Cave Hills Cemetery. Private gatherings are allowed but house rules must be followed.

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

Sleek urban condo near Kentucky Bourbon Trail

Discover the perfect blend of comfort and culture at Urban Bourbon Escape, a stylish and modern condo located in the vibrant heart of Louisville. Whether you're sipping your way through the Bourbon Trail or exploring the city’s historic charm, this sleek retreat is your home base for all things Louisville. Enjoy city views, walkable access to top attractions, a fully equipped kitchen, and a cozy space designed for couples or small groups to relax and recharge.

Location! Corner downtown condo!

Welcome to your stylish urban retreat in the heart of downtown Louisville! This studio corner unit condo boasts modern amenities and stunning city views through floor-to-ceiling windows. With an updated bathroom and kitchen, plus a location within walking distance to the KFC YUM Center, shops, and restaurants, this condo offers the perfect blend of comfort and convenience for your stay in Louisville. Book now and experience the best of Louisville living!

An Unhurried Stay in Butchertown · Steps from NuLu

Some places just make you feel held. This is one of them. A Jaclyn Journey Hospitality stay - set inside a 19th-century building on the edge of Louisville's Butchertown & NuLu neighborhoods. This apartment has been designed with the kind of care that's hard to put your finger on but impossible to miss. Every detail - from the original fireplaces to the lime-washed bedroom walls - has been chosen to make you feel genuinely at ease, not just comfortable.

Trendy Tiny Home w/ King Bed Loft

Unique experience in style! Enjoy a weekend or an extended stay at this charming carriage house just walking distance to popular restaurants, breweries and local shops. The location is perfect! Inside you'll find a fully equipped kitchen, bathroom, living room with a 55" smart tv, a dedicated work space/desk and a king sized bed in the loft. Guests will have privacy with self-check in smart locks and a dedicated parking space. We can't wait to host you!

Urban Enclave! Convenient 1800s brick shotgun.

Tasteful and comfortable historic shotgun-style home in the Original Highlands, a dynamic and convenient neighborhood. Great location for the Urban Bourbon Trail, and cultural venues including Yum Center, Center for the Arts, Paristown Point, Fair Grounds, Lynn Family Stadium, Ballet, Symphony, and Opera. Downtown, NULU, and Butchertown are adjacent. Smoke-free, naturist home. Please read all information regarding the space and guest access.

Stay in Historic Butchertown, Blocks From NuLu

With its prime location at 1025 E Main St at the intersection of Louisville's Butchertown and NuLu neighborhoods, you'll be blocks away from the city's most vibrant and exciting districts. With this beautifully renovated, designer-curated home as your base, walk to the area's trendiest shops and restaurants, sample local craft beers at one of the nearby breweries, or enjoy tastings on one of the many bourbon tours that the city is famous for.