Holiday rentals in St Matthews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Swanky Fully Equipped St. Matthews Apartment

Swanky East End Private Apartment. Completely renovated in 2018. New Shower, fully equipped kitchen. Huge walk in closest, FlatScreen TV and WIFI all included. Party Deck and Spaceous Living Room are ready for your Visit. King Bed and Queen Sleeper Sofa with spacious living, await up to 4 guests. Great venue for Trinity Football, University of Louisville Sporting events, Churchill Downs, or simply hitting the Bourbon Trail. 10 min. Uber to Whiskey Row and Distillery And/or and Nulu District

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.

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Prime central Louisville stay close to attractions

Discover this inviting two-story apartment located in the heart of Louisville. Perfect for families or small groups, this thoughtfully equipped home comfortably sleeps up to 7 guests with two queen beds and a sofa bed. Enjoy the convenience of a fully equipped kitchen, flat-screen TVs, and reliable high-speed WiFi. With comfortable living spaces, dedicated parking, and proximity to local attractions, this charming retreat offers an ideal blend of comfort and convenience for your next stay.

3 bedroom Crescent Hill cottage

Located on a wide, tree-lined avenue, this comfortable, stylish, and well-appointed Dutch Colonial is only a few minutes drive from Louisville's most popular entertainment districts, restaurants, and boutique shops along Frankfort Ave, Bardstown Rd, NULU and Downtown. Guests will enjoy the surroundings of one of Louisville's most desirable neighborhoods with Whitehall and Boyce College within walking distance and Garden Court, as well as historic Cherokee Park just a short drive away!

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

St. Matthews Gem *Pinball *Private Parking

Welcome to your home away from home! This charming 2-bedroom house is located on our property but offers private access and private fenced area. The house features a pinball machine, board games, a Nintendo Switch, and an Xbox—perfect for relaxing after a day of exploring Louisville. Tucked away on a quiet dead-end street, this home offers private driveway parking and convenient highway access.

The GiGi Airstream, Lakeside at Progress Park

Your stay in the Gigi Airstream at Progress Park will be anything but ordinary. Wake up to stunning views of the water, with the beach sand just outside your door. This 2022 Airstream Flying Cloud has all the bells and whistles and will ensure you are not roughing it while glamping in the city limits! We can't wait to host you! *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.