Smoking friendly holiday rentals in Louisville

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 Riverside Retreat - Your Coastal Getaway

Take it easy at this unique and tranquil getaway, perfectly situated with the Ohio River right in your backyard. Relax on the spacious back deck and enjoy stunning river views while unwinding in a peaceful setting. This home has been recently updated with a refreshed kitchen, flooring, modern lighting, updated bedrooms, and a renovated shower, making it a comfortable and inviting retreat for the duration of your stay. The Riverside Retreat is the perfect place to recharge and enjoy the scenery

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.

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)

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.

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)

Executive Studio | Free Parking | Downtown | 3F

IMPORTANT NOTE BEFORE BOOKING ‼️ Our studio is located in the heart of downtown Louisville, giving guests quick access to restaurants, nightlife, hospitals, conventions, and major attractions. Because of this prime city location, you may hear normal downtown noise, including traffic from nearby roads and the highway. For added comfort, we provide ear plugs and a white noise machine in the unit.

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.

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.