Vacation rentals in St. Matthews

4.95 out of 5 average rating, 346 reviews

A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.

Cabin in Louisville

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.

Guest suite in Louisville

A colorful living area is furnished with a patterned sectional sofa and a round glass coffee table. Natural light enters through multiple windows, illuminating the artful wall decor. A kitchenette area with modern appliances is visible in the background, enhancing the space's functionality.

4.94 out of 5 average rating, 290 reviews

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.

5 out of 5 average rating, 237 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

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.

A cozy living room is presented with a dark sofa facing a white-brick fireplace. Above the fireplace, a flat-screen television is mounted. Two armchairs flank the fireplace, while a small ottoman completes the seating arrangement. Light-colored drapes frame the windows, and artwork decorates the walls.

4.87 out of 5 average rating, 215 reviews

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

A private hot tub is situated on a paved area, surrounded by a wooden fence for added privacy. Colorful flower pots with blooming flowers are positioned nearby, complementing the fresh green grass. Two red chairs sit in the backyard, inviting relaxation.

4.99 out of 5 average rating, 262 reviews

Fall Haven - King Beds, Hot Tub

* 3 Bedrooms, 5 Beds, 2 Living Rooms. * 2 1/2 Baths * 2,500 sq ft (235sqm) * Private patio * (2) 60” Smart TV's w/Bluetooth speaker * Attached garage * Fully equipped Kitchen, upgraded appliances & sink * Flat screen TV in each bedroom & cable * Safe neighborhood * Close to local spots shopping malls in Louisville, gym, and St. Matthews *Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required*

4.92 out of 5 average rating, 147 reviews

Condo in Butchertown

Perfect Nulu Getaway w/ Best Location- low fees

You can’t find a better location in the city. Welcome to Lou Lou on Washington, our Nulu condo. We are located just steps away from the best food, drinks, and events in the derby city. We are located on a quiet street, only one block away from Main St. You can walk to breweries next door or even a soccer game at Lynn Family Stadium. The Yum Center is only a few blocks away, and we have one of the few properties located walking distance from Waterfront Park.

4.86 out of 5 average rating, 269 reviews

A modern kitchen area is highlighted by stainless steel appliances, including a refrigerator and microwave. An island with seating for two faces a cozy living space featuring a fireplace and natural light streaming in from large windows.

Apartment in Butchertown

The Point at Story and Frankfort Avenue

The Point is a spacious and completely renovated one bedroom (king) apartment. You will absolutely love the huge sectional couch while watching your favorite shows on the 65" smart TV. Unit very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.

A large wooden dining table is centered in the room, surrounded by wooden chairs. Two framed vintage world maps hang on the walls, adding an earthy tone to the space. A simple vase with greenery sits atop the table, enhancing the natural decor.

4.99 out of 5 average rating, 165 reviews

"The Brook" - Louisville

Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!

4.97 out of 5 average rating, 146 reviews

A two-story brick duplex is seen with white window trim and dark shutters. Lush green grass surrounds the property, complemented by neatly arranged rocks and low shrubs. The front door is accessible via a short set of steps, highlighted by sunlight filtering through nearby trees.

Condo in Crescent Hill

Hidden GEM, newly furnished in a safe, great area

Our “unit” is a great place to stay. Absolutely wonderful neighborhood with beautiful historic setting, cozy, safe and quiet. Short walking distance to many restaurants, shops, coffee houses. Majestic trees line properties and homes. Downtown & NULU 4 miles. Churchill Downs 10 miles, University of Louisville is 13 miles away. Golf & swim center .25 miles this. property is duplex. Very separate accommodations! Private!

4.91 out of 5 average rating, 140 reviews

A spacious living area features a comfortable sofa adorned with orange pillows, positioned on a patterned area rug. The open layout allows visibility into the kitchen, which includes wood cabinetry and dining space. A ceiling fan and light fixtures enhance the room's functionality.

Guesthouse in Louisville

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.

Guest suite in Louisville

A cozy efficiency room features a spacious bed covered in patterned bedding and a comfortable couch. A mirror and decorative artwork adorn the walls, with bedside tables and soft lighting from lamps. The en-suite bathroom is partially visible in the background.

4.96 out of 5 average rating, 164 reviews

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.

4.92 out of 5 average rating, 1,066 reviews

A blue carriage house is viewed from the driveway, surrounded by greenery and blooming trees. Steps lead to an upper balcony, offering outdoor potential. The driveway provides easy access to the garage, emphasizing a sense of space and privacy.

Guesthouse in Louisville

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

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Popular amenities for St. Matthews vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in St. Matthews

5 out of 5 average rating, 38 reviews

A charming two-story duplex in a peaceful neighborhood is framed by a lush garden. The exterior features yellow siding and dark wooden accents, while vibrant flowers and greenery create an inviting entrance. The separate entrances are highlighted, enhancing the sense of privacy.

Home in Crescent Hill

Little Gem off Frankfort Ave

4.85 out of 5 average rating, 262 reviews

A spacious bed is positioned in the center of the room, dressed in neutral bedding with a light blue throw at the foot. Two bedside lamps flank the bed, and a set of three cityscape prints hangs above, complementing the cozy atmosphere.

Apartment in Louisville

The Nest

A newly built two-story home features a light grey exterior with contrasting black roof accents. The front includes a small porch with a decorative entryway. The well-maintained lawn is bordered by shrubs, and a driveway accommodates multiple vehicles.

5 out of 5 average rating, 17 reviews

Louisville Retreat w/ Deck ~ 11 Mi to Downtown!

4.96 out of 5 average rating, 251 reviews

A spacious, walk-in shower is enclosed in glass, showcasing stylish Carrara marble walls and a built-in bench. Multiple shower fixtures, including an overhead showerhead, are visible. A plush gray towel is hung neatly on a glass panel, enhancing the modern and elegant design.

Condo in Saint Matthews

The Sweet Spot! - Live Like a Local

Apartment in Saint Matthews

An exterior view of the private apartment building features a welcoming entrance with a covered porch and an attractive staircase leading to the second floor. Surrounding greenery enhances the setting. Designated parking spaces are visible, with wheelchair accessibility indicated.

4.96 out of 5 average rating, 98 reviews

Swanky Fully Equipped St. Matthews Apartment

4.94 out of 5 average rating, 80 reviews

A riverside deck features two white Adirondack chairs positioned under a blue umbrella, providing shade and comfort. A vibrant area rug lies beneath, and the serene river view showcases gentle waves and lush greenery along the banks, creating a peaceful outdoor retreat.

Home in Jeffersonville

Beachfront River Cottage

Private room in Louisville

A bright bedroom features a queen-sized bed dressed in soft linens beneath sloped ceilings. A light blue dresser and a cozy armchair are positioned against the walls, with a small side table beside the bed. Natural light filters through a window covered by a half-shade.

4.97 out of 5 average rating, 1,442 reviews

Large room with bath in quiet neighborhood