Vacation rentals in Saint Matthews

4.83 out of 5 average rating, 126 reviews

A welcoming entrance is highlighted by a set of stone steps leading to a covered porch. Vibrant flowers enhance the greenery, while elegant architectural details are seen on the house. The porch features a decorative railing and a couple of seating areas for relaxation.

Apartment in Louisville

Highlands Harmony House - Near Cherokee Park

Upstairs; full sized Studio Apartment with large bedroom, kitchen, separated bath, private, big screened porch! The PRIVATE bathrooms are in the hall -3 feet from your bedroom/hidden behind privacy screens. "Yes, you can run to the bathroom in your 'all-together!" You'll love the kitchen and comfortable queen bed. Very cozy! Private screened porch overlooks our artistic/wooded backyard! Located on a quiet dead end street. Stroll our shady sidewalks to local bars coffee shops, restaurants etc.

4.74 out of 5 average rating, 286 reviews

A spacious waiting area is furnished with white modern chairs set around a sleek black coffee table. Light-colored flooring contrasts with darker accents. The background features a staircase leading to an upper level, providing access to additional areas of the salon and spa.

Apartment in Louisville

Grand Loft in Heart of the Highlands #4

Located in the Louisville's Historic Highlands neighborhood, and above of 5 Elements Salon and Spa our elegant unit is newly renovated and surrounded by tons of activities and scenery. - We're within walking distance to 20+ restaurants, 5+coffee shops, historic parks, trails, grocery stores, liquor stores, 20+ local shops and boutiques, bars/clubs and much more. - Safe/ neighborhood. - En suite washer/dryer - Hotel bedding, towels and amenities - Keyless entry - Parking Lot ( 1 Car)

4.86 out of 5 average rating, 182 reviews

The exterior of the river house features a large covered deck with a wraparound porch. Outdoor seating areas are visible, framed by greenery and shaded by a sloped roof. Glass doors open to the interior, allowing an inviting flow between inside and outside spaces.

Home in Elizabeth

Relaxing River House Retreat-Sleeps 10-12

Cozy newly renovated river house with ample entertainment space inside and out. Large covered deck with wrap around porch and a beautiful view of the Ohio River. 1 mile from Horseshoe Casino, just minutes from entertainment and amenities of downtown New Albany, IN and Louisville, KY. Less than 10 minutes from a local winery, 2 breweries, and Chariot Run Golf Course. Perfect for large groups or a romantic weekend getaway! Additional detached bonus bedroom. $100 extra per stay at guest's request.

4.93 out of 5 average rating, 196 reviews

Condo in Highlands

Large Townhouse, Walk to All! King beds, 2.5 baths

Large, 3 story townhouse sleeps 8 in 1600 sq. ft. Step out the door to best walking neighborhood in Louisville. Great coffee shop 150 ft. away, with a dozen places to eat, from fancy to casual, within the block. Parks, movies, live music are 10 minute walk or less away. 2 King bedrooms, each with full bath, 1 queen and 1 twin daybed w/ trundle. Fully equipped kitchen, 3 large smart tvs, wifi and cable! Kitchen fully equipped, from quality appliances to pots/pans/plates/cutlery/glasses/etc.

4.94 out of 5 average rating, 147 reviews

2 br home, walking distance to much entertainment

Home is located in the historic Irish Hill neighborhood, just a short walk to popular Baxter Ave and Bardstown Rd., famous for its restaurants, coffee shops and nightlife. Downtown is a quick drive away, lots of bars and distilleries are walking distance. Home built in 1879, entirely renovated with a modern kitchen, fully fenced backyard, private parking and a lovely fire pit. You will have a master bedroom with a king size bed and your own bathroom with jetted tub, very relaxing. Thank you!

Loft in Central Business District

A fully equipped kitchen features modern appliances, including a stainless steel refrigerator and a stove. A spacious island with bright yellow stools sits beneath pendant lighting. Exposed beams and a wooden floor complement the brick walls, while windows allow natural light to enhance the atmosphere.

4.93 out of 5 average rating, 91 reviews

Historic Nulu Loft| Downtown | Bourbon Trail

Our industrial loft is located in the historic Central Business District and NuLu area of Louisville. Local history mixes with a trendy and vibrant neighborhood known for its eclectic mix of art galleries, restaurants, and shops. The loft is situated close to all amenities and major attractions in downtown Louisville, including the popular Whiskey Row, Museum Row, Bourbon Trail and Louisville Slugger Field. We are a quick 12min drive to historic Churchill Downs, home of the Kentucky Derby.

4.84 out of 5 average rating, 89 reviews

A modern kitchen features sleek stainless steel appliances and a marble-topped island with seating for three. A textured brick wall adds character, while ample natural light fills the space through large windows, enhancing the contemporary design of this fully renovated area.

Home in Old Louisville

Exposition Center, Bourbon Trail, Downtown, & I65

Our guest will enjoy easy access to everything from this centrally located home. Right off of interstate 65. Conveniently located near downtown (2 miles), University of Louisville (1.1 miles), Cardinal Stadium (1.9 miles), Yum Center (2.3 miles), Churchill Downs (2.8 miles), Kentucky Exposition Center (3.1 miles), Louisville International Airport (3.9 miles), and many more local attractions. This home has been fully renovated and has two off street parking spaces in the rear of the house.

A spacious living area features a comfortable gray sofa adorned with decorative cushions, positioned next to large windows offering expansive water views. A glass coffee table rests on tiled flooring, surrounded by light-colored decor accents. Natural light fills the space, enhancing the serene atmosphere.

4.95 out of 5 average rating, 171 reviews

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!

4.92 out of 5 average rating, 106 reviews

The image shows a hot tub on a covered deck, with bubbling water and a view of a backyard fire pit area below. Four blue Adirondack chairs surround the fire pit, which is under a canopy of string lights amidst lush greenery.

Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

The kitchen features wooden cabinetry and a double sink, with a plate of cookies resting on the counter. Breakfast items are displayed, while a dining area with a round table and four chairs is visible in the background.

4.72 out of 5 average rating, 29 reviews

The Shaded Retreat

Kick back & relax in this calm, stylish space. Designed for long-term stays. Traveling medical workers & project work teams will find this a perfect fit. Flexible sleeping arrangements: accommodates 5 extra large twin beds and 1 queen bed. Deep discounts for longer stays. The second bathroom is set for renovation but is fully functional. It's connected to the laundry room and back door. For guest with pets it a great space to clean paws before entering the main house.

An open loft bedroom features a spacious bed dressed in soft linens with decorative pillows. A large window allows natural light to flood the room, while a ceiling fan helps with airflow. A comfortable seating area is visible in the background.

4.91 out of 5 average rating, 157 reviews

New Signature Highlands Home- steps away from…

Welcome to our new to AirBNB Highlands home. Recently redecorated and updated, this home is steps away from many incredible local restaurants, bars, and shops. Less then one mile to Cherokee Park. Less then five miles to Churchill Downs, NULU, and the airport. You simply can’t beat this location. Safe, family friendly neighborhood with swing-set in the back yard (high chair, pack and play, toys, and more available upon request).

4.94 out of 5 average rating, 143 reviews

An outdoor area features a cozy gazebo with soft lighting, surrounded by lounge furniture. A hot tub with illuminated water sits nearby, while decorative stones and plants add to the tranquil environment. Fenced in for privacy, this space is ideal for relaxation.

Home in New Albany

king bed and oasis backyard with hot tub

11 miles to Derby. Come enjoy our newly decorated house with a hot tub, gazebo outdoor fun area and lounge furniture and wood burning fire pit. The idea is to both indoor and outdoor give you a great experience that not everyone offers! We sleep 4 adults comfortably in our 1 KING size bedroom and 1 QUEEN size bedroom. We're located in a quiet neighborhood with a fully fenced in backyard and we're Pet Friendly with a fee!

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Popular amenities for Saint Matthews vacation rentals

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Stay near Saint Matthews's top sights

Mall St. Matthews130 locals recommend

Oxmoor Center99 locals recommend

Seneca Park54 locals recommend

Whole Foods Market52 locals recommend

Simply Thai51 locals recommend

Trader Joe's44 locals recommend

Other great vacation rentals in Saint Matthews

5 out of 5 average rating, 33 reviews

Farm stay in Crestwood

Maple's Place - *charm*country*hot tub*bourbontour

4.97 out of 5 average rating, 38 reviews

The exterior of the house features a spacious back deck overlooking a well-maintained yard. A fire pit with red chairs is positioned in a circular gravel area, inviting gatherings. The two-story structure showcases multiple windows and a sloped roof, blending comfortably with the surrounding landscape.

Home in Elizabeth

The Getaway

A bright and open dining area features a large wooden table set for meals, surrounded by light-colored chairs. The kitchen, equipped with modern appliances, is visible in the background. Natural light floods in through large windows, enhancing the welcoming atmosphere of the space.

5 out of 5 average rating, 12 reviews

Bourbon City Bungalow

Condo in Central Business District

An open living area showcases a wooden dining table set for six, with glassware and tableware arranged. A staircase with a modern railing leads to a balcony area overlooking the space. A sleek kitchen with white cabinets and an adjacent cozy seating arrangement is visible.

4.9 out of 5 average rating, 67 reviews

Main Street Farmhouse! City Retreat by Hollyhock

Farm stay in Simpsonville

4.91 out of 5 average rating, 64 reviews

Spacious Home with Beautiful Views

A spacious basement area is furnished with a large, dark leather sectional couch adorned with decorative pillows. A round wooden table sits at the center, while a wet bar and wine glasses are visible in the background. Natural light filters through a small window.

5 out of 5 average rating, 17 reviews

Bourbon Country Cottage

4.95 out of 5 average rating, 699 reviews

A designated fire pit area is surrounded by ten wooden adirondack chairs, arranged in a circular formation around a stone circle. Lush green grass and trees provide a serene backdrop, while a cabin is faintly visible in the distance.

Farm stay in La Grange

The Cottage at StoneLedge 2 bedroom/1bath