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!

Weekly Downtown Penthouse Loft- Parking & Elevator

Flexible start dates available for extended stays — message me if your dates don’t align perfectly. Now accepting January–February weekly stays — ideal for extended work travel, relocation, or temporary housing needs. This downtown penthouse loft is optimized for weekly stays and designed for guests seeking a quiet, comfortable, and fully equipped home base in the heart of the city. Perfect for extended business travel, corporate housing, medical professionals, relocation, or insurance stays.

Band Camp!

Welcome to our incredible 7 bed, 3 bath Louisville Airbnb! Centrally located, this spacious home is the perfect base for your Kentucky adventures. Situated close to the airport, track, fairgrounds, and downtown, our property offers convenience and easy access to all the city has to offer. With its comfortable bedrooms, well-equipped bathrooms, and ample space for large groups, our Airbnb provides a comfortable and enjoyable stay for every guest. Book now and experience the best of Louisville!

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

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.

12 Guest/Top Area /Families/Park

Welcome to our Family Airbnb 1- Great Location in residential neighborhood 2- 20 Min to Kentucky Derby Museum 3 - 20 Min to Louisville Mega Caverns 4- 15 Min Evan William Bourbon 5- 20 Min Churchill Down 6- Designed for 2 guests (3 Queen Bed, 1 double Bunk bed, 1 Queen Air Mattress) 7- Free Parking (2 Cars Inside and 2 Cars Outside) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Quiet and Safe Area 11- Private Patio 12-24/7 Available Host 13- 2 Smart TVs 14- Laundry In Unit

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!

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)

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: Black Walnut

🌲 5-Acre Creekside Camping: Black Walnut 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.

Central Location. Expo cntr, UofL, Churchill Downs

Professionally updated interior in this quaint 2 bedroom home, plus bonus room with futon and free garage parking. Centrally located near the airport (5 min), Churchill Downs, UofL, iroquois amphitheater and more. 10-15 minute drive to downtown. Walk to great restaurants and our favorite local coffee shop.

The Offbeat Oasis in New Albany

Be our guest at the Offbeat Oasis, in the sweet, small town of New Albany, Indiana, which is right across the river from the fun and bustling city of Louisville, Kentucky and 10 minutes away from Churchill Downs! We hope our guests chill and have fun in our quirky, relaxing space!