Smoking friendly vacation 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

+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 +4 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.

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

Downtown Penthouse Loft- Free Parking & Elevator

A warm, comfortable downtown loft with garage parking — ideal for work trips, longer stays, or a quiet city escape. It’s a true city loft — open, airy, and easy to live in while still being right in the middle of everything. Located in a historic downtown building, the condo sits on a quiet residential floor, making it a calm, comfortable place to come back to after a day out. Secure garage parking and elevator access make coming and going simple

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)

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!

Not Everything is Black &White Rooftop Penthouse

Enjoy a stylish experience at this centrally-located penthouse with a unique private rooftop. A real urban vibe in a very cool little city on a quiet yet vibrant block. Very walkable. Close to restaurants, live music, comedy clubs, museums, sporting arenas, yum center, whiskey row, speak easies. Short Uber ride to Churchill Downs, the expo & SDF

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.