Smoking friendly holiday rentals in Jefferson County

Sweet Highlands Victorian 2Blocks off Bardstown Rd

My place is close to nightlife, public transport, parks, and the city center. You’ll love my place because of the high ceilings, the coziness, the comfy bed, the light, and the kitchen. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups. Nulu and downtown are minutes away. You can stroll down our lovely sidewalks and look at the beautiful Victorian houses and trees, enjoy some great food, with lots of quirky shops just footsteps away. Enjoy!

3600SF~2 Kitchens~Hot Tub~Game Room-Backyard

+Sleeps 18 +Large Fenced Backyard- Gazebo, Hot tub, Fire pit, Grill, Trash pong, Cornhole, Giant connect 4 +Game room including: Pool, Ping Pong, Foosball, and Poker tables with 2 smart tv’s +Kids room with NINTENDO SWITCH, 8 controllers, and 2 standing arcade games +2 Fully stocked kitchens +2 living rooms +Top and bottom floor are separated by door for privacy +High end memory foam mattresses +2 sets of washer/dryers +6 driveway parking spots +11 Smart TV’s +Kid friendly amenities

The Camp Taylor Cottage Close to Airport/ Downtown

We’re delighted to host you at this beautifully updated home, thoughtfully refreshed throughout to ensure a comfortable and memorable stay. From the moment you step inside, you’ll notice the attention to detail and inviting atmosphere designed with our guests in mind—perfect for unwinding, and feeling right at home. The cottage features 2 comfortable bedrooms, 4 beds, and sleeps up to 8 guests. Guests will also enjoy the spacious-oversized shower, perfect for unwinding after a long day.

Executive Studio | Free Parking | Downtown | 3F

Experience the vibrant heart of Louisville in this stylish loft apartment in the historic medical district. Just steps from the YUM! Center and Kentucky International Convention Center, you’ll have easy access to numerous attractions. Explore nearby distilleries, savor meals at trendy restaurants, and discover fascinating museums—all within reach. Whether you’re here for an event or to soak up local culture, this prime location is your gateway to an unforgettable adventure in the city!

Walk to Bourbon Trail | NULU Gem | Gated Parking

Stay in the heart of NULU—this modern ground-floor condo puts you steps from Louisville’s best restaurants, bourbon stops, and local shops. Walk to favorites like Angel’s Envy and Rabbit Hole Distillery, enjoy all the NuLu dining, or head downtown in minutes for concerts, games, or events. The condo is comfortable, quiet, and thoughtfully set up—ideal for couples, solo travelers, or business stays, with gated parking, fast Wi-Fi, and everything needed for short or extended stays.

Airstream Farm Stay Getaway!

Enjoy some time away on a farm in a customized remodeled 1977 Airstream Sovereign! Top of the line details inside - a warm and cozy farm outside! Spend time with the horses, pigs, chickens and cats during your visit! Whether it is picking flowers in the garden or starting a fire in the solo stove! We have everything you need to reconnect to nature in Luxury! PLEASE TAKE NOTE! The toilet is a composting toilet. Special instruction for use in manual. EASY AND CLEAN TO USE.

The Rickhouse ~ NULU ~ Bourbon Enthusiast’s Oasis!

Rickhouse: A structure designed to store and age distilled spirits. Sparked from a passion for fine spirits and the idea that a home can contain all the makings to craft the perfect cocktail, the Rickhouse was born. Featuring chesterfield leather seating, a vast collection of cocktail glasses, regulated 4-tier humidor and spirits-centric art, it strikes the perfect match of comfort and eccentricity. Cheers and enjoy The Rickhouse!

Blush & Whimsy Penthouse Loft with rooftop terrace

A penthouse Loft. Unique among short term rentals. A fair price for ultimate luxury. Luscious fancy folded towels, yummy robes, a candy on your pillow. Unbelievably comfortable in a high end setting. Fabulous location, close to everything. Restaurants, live music, the bourbon trail, whiskey row, Muhammad Ali, Speed, Slugger museums, all within walking distance. Convention Center, medical centers within 2 blocks.

Barks & Bourban Your derby city retreat

Welcome to your tranquil retreat in Louisville, KY! Located at 2830 Esther Blvd, our dog-friendly home offers peace and convenience. Nestled in a safe, upscale neighborhood 10 mins from downtown, enjoy 3 bedrooms, 2.5 baths, fenced yard with dog door. Nearby bourbon distilleries: Evan Williams (5 mi), Bulleit (8 mi), Angel's Envy (4 mi). Explore Louisville, largest, Cherokee Park scenic trails (3 mi)

Affordable luxury 5 mins from dwtn Louisville

NO NEIGHBORS, NO NEIGHBORS, NO NEIGHBORS! Welcome to Wall Street Suites, a modern and stylish 2-bedroom, 2-bath getaway designed for travelers who want privacy, comfort, convenience, and a touch of luxury. With no neighbors, secure parking, and a location just 5 minutes from downtown Louisville, this space offers the perfect balance of privacy and access to the city’s best attractions.

Beautiful house in suburban neighborhood

Safe space to relax and have a good time with your loved ones. Located in a nice neighborhood with swimming pool, basketball and tennis court, it’s the perfect place to enjoy time with your family or friends. Only 15 mins away from downtown Louisville, it’s close to restaurants, grocery stores and a movie theater. Peace and fun all in the same place!

5 acre Creekside Camping: Willow

🌲 5-Acre Creekside Camping: Willow Nestled along a peaceful creek and bordering Jefferson Memorial Forest—Louisville’s largest park. Escape the city and camp under the stars on our 5 wooded acres, seamlessly connected to thousands of acres of pristine woodlands. Wake up to deer, turkey, and eagle sightings—all just steps from your firepit.