Holiday rentals with breakfast in St. Matthews

Parkside Retreat

Situated off of a parkway with mature trees lining the street, this parkside retreat is close to most everything. We are a short drive to Churchill Downs, Downtown, the Airport. Our home sits on one of the most beautiful streets in the entire neighborhood. We are 7 houses from Iroquois Park. It is terrific for walking, hiking, or just having a picnic. We have a privacy fence with a jacuzi tub on the deck. Many updates make this home the perfect choice to relax after a day of fun activities

Downtown Retreat | Walk to Dining & Shopping

🌆 Just steps from local restaurants, boutiques, historic sites, and the scenic Ohio River ☕ Start your day with our fully stocked coffee bar—complimentary snacks included! 🚶‍♀️ Walk to the farmers market, riverfront trails, and weekend festivals 🎰 Only minutes to downtown Louisville and Caesars Casino 🛏️ Spotless, secure, and thoughtfully designed for a comfortable stay 🚗 Easy, convenient parking + quick self check-in 💬 Hosted by responsive locals ready with personalized recommendations

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Bourbon City Loft - Free downtown parking!

If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

Relaxing Oasis - Churchill Downs

Fantastic Location! This newly updated home offers a 5-minute walk to Churchill Downs and the University of Louisville, 5-minute drives to the airport and Fairgrounds/Exposition Center, and 10-minute drives to trendy NuLu, Highlands, and Germantown neighborhoods. This space will offer the best of what Louisville has to offer. THIS AIRBNB PROPERTY HAS A ZERO TOLERANCE FOR PARTIES OF ANY KIND. THE POLICE WILL BE CALLED AND THERE IS A $500 FEE LEVIED ON GUESTS FOR HOSTING PARTIES

Cottage Park Carriage House. Rest w/Hollyhock

The Carriage house is located behind a historic mansion in beautiful Crescent Hill. Situated next to a park, this ideal location is still one block away from Frankfort Ave. shopping & dining, conveniently located near downtown, Churchill Downs, & four blocks from the Largest park in downtown Louisville. Newly designed and renovated-includes two separate bedrooms, office area, full kitchen, bathroom, & laundry. Free wifi, & parking. Refresh and relax in this satisfying getaway!

Sunny Clifton Loft

Recently renovated studio apartment with loads of natural light, steps from award-winning local restaurants, bakeries, bars, and housed above our independent record store. We do our best to AirBnB ethically & responsibly.. Revenue from this unit helps to 1) keep on-site residential rents affordable & increase-free 2) maintain the historic building & protect it from outside development while 3) help us steer our future as a brick and mortar independent business.

Trendy Tiny Home w/ King Bed Loft

Unique experience in style! Enjoy a weekend or an extended stay at this charming carriage house just walking distance to popular restaurants, breweries and local shops. The location is perfect! Inside you'll find a fully equipped kitchen, bathroom, living room with a 55" smart tv, a dedicated work space/desk and a king sized bed in the loft. Guests will have privacy with self-check in smart locks and a dedicated parking space. We can't wait to host you!

COZY! Minutes from Louisville. No cleaning fees!

NO CLEANING FEES!Relax in this modern yet cozy space. (2)Queen beds/bedrooms. NOTE: We too reside in upper level but will not invade your privacy. NO SHARED LIVING SPACE. 6 minutes to 2nd St bridge/65S to downtown Louisville or 2 minutes to East End Bridge (265E) to Louisville LOU (SDF) Airport 20 min CHURCHILL DOWNS 21 min Highland Festival Grounds/Ky Expo Ctr 18 min LOU Waterfrnt 12 min KFC YUM Ctr 12 min Ky Kingdom 16 min