Holiday rentals with outdoor seating in Highlands

Charming Highlands Home | Walk to Everything

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

2 br home, walking distance to much entertainment

Home located in the historic Irish Hill neighborhood, just a short walk to popular Baxter Ave and Bardstown Rd, famous for its restaurants, coffee shops and nightlife. Downtown and Nulu are a very short drive away, many great bars and distilleries are walking distance. Home built in 1879, entirely renovated with a modern kitchen, fully fenced backyard, private parking and fire pit.Master bedroom has a king size bed and it’s own bathroom with jetted tub. We look forward to your visit, thank you!

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Shotgun Rye is ready for Kentucky Derby 2026!

Shotgun Rye is ready to host your stay in Louisville! Located close to everything cool in Germantown and Highlands area! People visit for Bourbon Tours, Ky Derby, Conventions, Expo Ctr, UL graduations and sporting events, live music and so much more! Completely remodeled with all the modern conveniences & a comfortable, casual touch. But with so much to see and do in Louisville you’ll load up your itinerary with unforgettable experiences. Great location walk to bars, restaurants and shopping!

4th Street Suites - Comfortable King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

The House with the Orange Door

Located near Churchill Downs, UofL, downtown, the Convention Center and Fairgrounds, and a short distance to restaurants, bars and coffee shops. This single family home offers two bedrooms with queen beds and a pull-out couch in the living room. Enjoy coffee or a relaxing evening cocktail on the back deck. The kitchen is fully equipped and the open living space provides a great area for socializing. Locally made art and decor is on display, adding to the uniqueness of the space.

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.

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

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.

Eco+ guest suite in the center of all the fun

Hip modern amenities meet historic home in Shelby Park. A quick drive to everything in the urban core - Downtown, Nulu, Old Louisville, the Highlands, Germantown, and more. Easy access to the airport, to boot! We are pet friendly home, but require your pets be registered on the booking. We want your pets (and ours) to be as safe and comfortable as you are, and the fee covers additional costs to complete allergen level sanitization.

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.