Apartment vacation rentals in Highlands

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Highlands Happy Place, Downtown, EXPO, highlands

Look no further, you have found Your HAPPY PLACE! Welcome to the Cherokee Triangle, the safest & most walkable neighborhood close to downtown Louisville! This charming apt. home is the entire 2nd floor of this adorable cottage style Highland's home. 3 bedrooms and 2 baths - this home contains 4 beds, 1 King, 1 Queen, 1 full and 1 twin bed (plus 1 twin roll away bed). Great for business travelers, or 4 or 5 friends/family members that all need their own bed! You have found your HAPPY PLACE!

Cozy Craftsman in Historic Highlands - 1920s Apt

Step into the warmth and character of this beautifully restored 1920s bungalow in Louisville’s beloved Historic Highlands. Thoughtfully updated for modern comfort while preserving its vintage charm, this space offers the perfect mix of history and hospitality. You’ll be just steps from the city’s best local restaurants, cafés, and boutiques. Downtown Louisville and NuLu are just minutes away. 5 ml to Churchill Downs Make this gem your home base for experiencing the best of Louisville

Vintage yet Modern Highlands home! Walk to venues!

Spacious 1st floor apartment in a Victorian duplex home in the heart of the Highlands/Germantown. We're ready to host for short, mid & long term! Because of our close proximity to Louisville’s vibrant nightlife, eclectic dining scene & shopping it’s no wonder visitors flock here to get a taste of something amazing! Perfect place for your Ky Derby home base! Walk down to the hottest Arts & Music venue in town-Old Forester Paristown Hall! Don’t forget about the Bourbon tours & new breweries!

Highlands Zen Oasis • Comfy, Clean & Cozy

Awesome Sweet Spot of a Louisville Location! This PRIVATE APT. with SELF CHECK IN + FREE PARKING is in a beautiful, safe neighborhood in the historic Highlands. Quick 2-min walk to magnificent Cherokee Park OR charming Bardstown Road - a multitude of eclectic galleries, bars, restaurants & shops to explore! Conveniently (5-10 min) located to Churchill Downs, Downtown Louisville, Louisville Seminary, NuLu, UofL, Bellarmine, Fair & Expo Center, Yum Center, Waterfront & the Airport⚜️

4th Street Suites - Ali King Bed Suite

Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

Highlands Airy Retreat- No Hassle Checkout

Welcome to "Birdie". The cutest, most conveniently located home in the city. From head to toe, Birdie is decked out with all the ingredients for a fun, relaxing Louisville stay. Occupying the 2nd floor of a beautiful Victorian home, Birdie is walking distance to restaurants and the urban bourbon trail, as well as hospitals and downtown businesses. The location truly can't be beat! Drive or Uber to the Yum center, NULU, Lynn Family Stadium, and the waterfront in no time.

Chic Apt – Heated Pool & Hot Tub Near 4th St Live!

Enjoy all of what Louisville has to offer with this luxury apartment perfect for 4! With a king memory foam bed and a queen memory foam sleeper sofa, you can enjoy a peaceful nights sleep and wake up to complementary coffee and a sunrise over the city skyline! Enjoy the plethora of activities and restaurants all within walking distance, including 4th St. Live! End the day with a virtual golf game, hit the gym, or relax with a movie. Book your stay with us today!

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

The Point at Story and Frankfort Avenue

The Point is a spacious and completely renovated one bedroom (king) apartment. You will absolutely love the huge sectional couch while watching your favorite shows on the 65" smart TV. Unit very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.

Sun-filled Phoenix Hill Studio

Located in the Phoenix Hill neighborhood, it's a short 11 minute walk to East Market District restaurants and attractions or a 15 minute walk to Gravely and other Original Highlands destinations. 11 minute drive to Churchill Downs 5 minute drive to the Highlands 4 minute drive to East Market restaurants and shopping. Ample Lyft and Uber drivers in this neighborhood to take you anywhere you want to go. .

Walk to Bars & Restaurants | 1BR Highlands Stay

Prime Location in Louisville’s Most Walkable Area! Just 7 minutes to the KFC Yum! Center with dedicated parking and steps from hundreds of shops, bars, and restaurants. This comfortable, well-equipped home offers exceptional value for your stay. Enjoy: •Easy self check-in with keypad •Photo-guided check-in instructions •Stocked kitchen for cooking •Roku TV & free Wi-Fi