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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

The House with the Orange Door

Near Churchill Downs (7mins) UofL (5mins) downtown (10mins) Convention Center (10mins) Fairgrounds (4mins), and close to restaurants, bars and coffee shops. The home offers two bedrooms with queen beds and a pull-out couch in the living room. Enjoy coffee or a relaxing evening 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. No local bookings please!

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.

Bourbon Trail Spacious Backyard NEW HotTub Grill!

The Burnt Barrel – Your vibrant Louisville getaway in the historic Shelby Park neighborhood! Perfect for couples, business travelers, or event visitors. Enjoy high-speed Wi-Fi, a dedicated workspace, fully equipped kitchen, & a NEW hot tub & grill. Just minutes from Whiskey Row, the Urban Bourbon Trail, Churchill Downs, NuLu, UofL Health, and the Convention Center. Explore iconic spots like Old Forester, Angel's Envy, & Evan Williams — all within 10–15 minutes. True Louisville charm awaits!

The Burb Inn - Nulu & Downtown *w/Firepit*

The Burb Inn is a hip place to stay in the Phoenix Hill/NULU district of Louisville. Easy access to top rated restaurants, bars, and attractions. Great place to host a group of friends, family or smaller bachelor party. Includes private parking, yard & fire pit. Upon entering there is a living area perfect for entertaining with 16’ ceiling & sleeping loft above the kitchen area. Upstairs has two bedrooms with queen beds each with private half bath. There is a separate private shower room.

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT

- 3 min drive to U of Louisville - 5 min drive to KY Expo Center - 7 min drive to Louisville Zoo This gorgeous 3-bed, 2-bath house is less than 4 miles from downtown Louisville. With its fully-equipped kitchen, spacious rooms & completely renovated kitchen, the house is the perfect base for large groups wanting to explore the city. Enjoy the wide variety of shops, restaurants, & bars nearby. Kentucky Derby fans love the close proximity to Churchill Downs. No Locals Please

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

Derby City Bourbon Bungalow - by Germantown & UofL

This charming bungalow is fully renovated and well appointed for guests. It's conveniently located near all of the hot spots in Louisville. We are just minutes from Churchill Downs, Germantown, NuLu, Louisville Airport, the Yum! Center, Slugger Museum and Waterfront Park. There are countless restaurants, parks, shops and bars nearby. Relax and enjoy the many amenities in and around our home. We have 3 bedrooms and 2 full bathrooms.

Spruced-Up Shotgun, Steps to Logan St Market

Recently renovated full 2 bed/2 bath house in historic Germantown. Guest will enjoy a full kitchen with all utensils and appliances provided. Living room has 55' TV with plenty seating and light. Each bedroom has double bed with linens, dressers, nightstand, and closet. Full bathroom connected to each bedroom with towels and toiletries. Front and back door uses coded Yale locks. Security cameras on front and back doors.

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.

Luxury Waterfront w/ Sauna HotTub Cinema Pet Views

Explore a stunning luxury riverfront retreat on the Bourbon Trail with sweeping Ohio River views. Just 15 minutes to Churchill Downs and minutes from downtown Louisville, this private home sleeps 12 and features a hot tub, sauna, theater, game room and expansive deck. Enjoy bourbon tastings, sunset fires by the river and elevated comfort—perfect for Derby weekends, family gatherings and unforgettable group escapes.