Condo holiday rentals in Kentucky

★ Victorian Louisville ★ 1000 sqft Glassworks Loft

Fresh, modern and sleek 950 SqFt loft style unit. Constructed inside the historic glassworks building, this condo is one of the most unique in the city. You will be amazed by the style, but also the amenities nearby. With a 2 minute walk to Museum row, and a 7 minute walk whiskey row, the convention center, the YUM! center and the center for the arts - everything is nearby. With Wifi, Netflix, and Hulu provided you have everything you need. The perfect spot for relaxing or going out on the town

Location · Value · Laundry

The Sweet Spot! - Live Like a Local

Live like a local in one of Louisville’s most sought-after neighborhoods, young professionals and families alike. Rich in history and surrounded by wall-to-wall dining, shopping, and entertainment, this vibrant area is known for its charm, energy, and premium appeal. Originally built as a single condo over two decades ago, the owner later acquired the neighboring unit and completely reimagined the entire second level. The result is a thoughtfully crafted space that truly feels like a retreat.

Value · Family · Hot tub

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

Family · Location · Sleep quality

“New” Downtown Modern Luxury Townhouse!

Welcome to one of the premier new locations to stay right in the heart of Elizabethtown! This modernly decorated two bedroom luxury townhouse has many features you won’t find at other sites at an incredible and convenient location. You can work from the townhouse in a dedicated office area with high speed internet. You can relax in the open living area on the second floor or on the covered deck. The place also features a rooftop terrace.You can walk to a lot food and fun! Enjoy it!

Family · Location · Kitchen

The Derby City Loft, luxury, walk to museum row

Located in historic downtown Louisville the Derby City Loft is a show stopper! This PENTHOUSE luxury condo offers stunning views and high end living. The open floor plan boasts 3 queen beds, curtains can be pulled to make it a 2 bedroom. Plus the oversized sectional sofa may sleep 2 comfortably as well. Fully stocked kitchens and bathrooms with everything! This home was designed and styled with your comfort in mind, kick back, relax and enjoy high style living at the Derby City Loft.

Location · Family · Nearby

Keenland Special- 2 Mi. to Downtown - Rupp - UK

📍 Prime Location - Chevy Chase / Ashland Neighborhood 🚶 0.05 mi to restaurants, breweries & coffee shops 🌳 1 block to Woodland Park 🎓 1 mi to UK & Downtown 🏀 2 mi to Rupp Arena & Kroger Field ✈️ 5 mi to Blue Grass Airport Perfect for UK game days, concerts, bourbon tours, business travel, or a weekend getaway while enjoying one of Lexington's most walkable neighborhoods. 🏡 Renovated 1900s home with a Speakeasy & Flapper theme 📺 Smart TVs • 🛜 Fast Wi-Fi • 🚗 Plenty of parking

Location · Family · Cleanliness

Cozy studio in The Foxbriar - Downtown

Home of the former Foxbriar Inn, this condo is located inside a beautiful historic building. This space is great for your weekend away or a longer term stay. Exposed brick and high ceilings make it a charming and cozy experience. Enjoy the perks of walking to lots of great restaurants, specialty shopping and boutiques. We are just seconds from a beautiful stroll along the River. Bakery and coffee shop underneath. Enjoy brunch on the weekends or a sweet treat anytime in the week.

Value · Family · Checkout

Stylish Condo on Broadway

Experience the beauty of downtown Paducah at our stunning historic condo. Curated by local interior designer, this space boasts stylish design elements combined with modern amenities to create a truly unique stay. You'll love the large windows, soaring ceilings, and original hardwood floors. You'll also have 24 hour access to a state-of-the-art gym. With its prime location overlooking Broadway, you'll be just steps away from top dining, shopping, and entertainment options.

Value · Family · Solo travel

Lexington's Artistic Bunker / 1BR Downtown Condo

Lexington's Artistic Bunker is a space carefully crafted with amenities aplenty! Perfect for the traveling business, medical, or education professional, the guest visiting family/friends, or those experiencing the beauty of the Bluegrass, this modern condo is located in the heart of downtown Lexington. Featuring one bedroom, concrete floors, original murals, walk-in shower, and vaulted ceilings this high-end industrial condo will leave guests satisfied from every angle.

Family · Value · Check-in

Charming Penthouse/Rooftop Patio/Downtown

Unwind and enjoy sweeping river views on the rooftop patio while staying in this private 5th floor Penthouse apartment. Intentionally designed and decorated. Features include: a full upscale kitchen, open concept living and dining area, cozy King bed, large plush bathroom, and laundry in the suite. Whether visiting for work or pleasure, this spacious urban suite is located on The Bourbon Trail and within walking distance to Louisville's most popular venues!

Family · Location · Check-in

Downtown Penthouse Loft- Free Parking & Elevator

A warm, comfortable downtown penthouse 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

Value · Family · Check-in

RiverSuite1-Experience the view w/a group of 10+

Relax by the river in this beautiful space that showcases a huge living room with a panoramic view of the Ohio River & Bridge. Walkout onto the enormous, covered deck to relax while you take in the mesmerizing view. Located less than a 1/2 mile away from the Downtown (DTR) where you can stroll along historic brick streets as you dine and shop at several unique spots. The view is often said to rival the world’s most beloved views.

Value · Location · Access