Family-friendly 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.

Carriage House - Crescent Hill (Frankfort Avenue)

Newly constructed carriage house in a charming historic community. Enjoy your own private getaway in the heart of Louisville's Crescent Hill neighborhood. This carriage house features an open kitchen / living concept with two private bedrooms (each has a comfortable queen bed) and a shared bathroom. In close proximity to local shops, restaurants, coffee shops and parks. Located less than 5 miles from downtown Louisville, less than 6 miles from the Expo center, less than 7 miles from the airport

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

Your Cozy Louisville Hideaway in the Highlands

Newly renovated basement apartment in the Highlands. Safe, quiet neighborhood, dedicated off street parking and proximity to some of the best food, shopping and entertainment Louisville has to offer. Easy access to all things Louisville! -Downtown Louisville -Churchill Downs -YUM! Center -Olmstead Park -NULU -Urban Bourbon Trail -Bardstown Road -Germantown -Thriving Music and Art scene -Louisville Convention Center -Great dining and breweries -Louisville International Airport -UofL -And more!

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.

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Parkside 3 Bedroom apartment

This apartment is in a growing and diverse part of Louisville. It is located in the Shelby Park neighborhood just a few blocks from Old Louisville and a few blocks from Germantown. The house has been recently renovated and it is beautiful. Virtually everything in the apartment is new. The bathroom feels like a spa with a freestanding modern tub and a walk in shower with double shower heads and a tankless hot water heater for unlimited hot water.

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

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.