Smoking friendly holiday rentals in Jefferson County

Luxury Urban Loft on Market Street | Bourbon Trail

NEW! | Stunning Nulu Loft on Market St – Walk Everywhere (92 Walk Score!) Step into a stylish, spacious loft in the heart of Nulu, Louisville’s most vibrant neighborhood. Located directly on E Market St, this multi-level retreat puts you steps from top restaurants, bourbon bars, galleries, and boutiques—perfect for exploring. With private entry, full access to two expansive floors, and thoughtfully designed spaces, this loft is ideal for groups, couples or anyone wanting a true urban experience.

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!

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.

The Farm at Grace Hill - Luxury Airstream

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.

Private Hiking Trails | 9-Person Hot Tub

Sleeps 12 • Private Hiking Trails • Fire Pit • Dog Friendly • Near Louisville • Family Gatherings • Group Trips * Downtown Louisville (15 min) * Churchill Downs (15 min) * Kentucky Derby Museum (15 min) * Louisville Mega Cavern (20 min) * Louisville Zoo (20 min) * Louisville Slugger Museum (20 min) * Big Four Bridge (20 min) * Huber’s Winery (25 min) * Squire Boone Caverns (15 min) * Caesars Southern Indiana (20 min) * Valhalla Golf Club (25 min) • French Lick Resort (45 min)

NEW Family Resort Home with Saltwater Pool & Games

Ultimate group getaway for up to 20 guests near Kentucky Convention & Expo Centers. This expansive home offers a private oasis with a heated saltwater pool, hot tub, huge game room, and fully-fenced backyard on 2/3 Acre. Perfect for large families or retreats, featuring a dedicated kids' play area, fully stocked kitchen, and high-end memory foam mattresses for a comfortable stay. Enjoy resort-like amenities and ample entertainment just minutes from major attractions.

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!

The Audubon Derby Retreat

Welcome to your Derby home in the heart of Audubon Park, one of the area’s quietest and most charming neighborhoods. This cozy and comfortable retreat has been thoughtfully designed with Derby travelers in mind, offering the perfect place to relax and unwind. Located less than 10 minutes from the Derby festivities, you’ll be close to all the excitement while enjoying the peace and character of this beautiful community.

Great for Short or Long Stays: Downtown New Albany

LOCATION: Prime spot! Enjoy all that New Albany has to offer. Location is walking distance to various dining options, farmer's market, shopping, and the riverfront. THE UNIT: This unit is super clean and has modern and up-to-date amenities. Very safe neighborhood and convenient free street parking. FLEXIBLE BOOKING OPTIONS: This unit is great for long-term stays, work visits, or quick getaways.

The Signature Downtown Jeffersonville Getaway

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!