House holiday rentals in St Matthews

A spacious living area features a comfortable sectional sofa and a large, cozy bean bag styled cushion. Decorative lighting provides a warm glow, and a stone fireplace is centered on a light blue wall. A patterned area rug adds color, while large windows invite natural light.

4.99 out of 5 average rating, 169 reviews

Cozy cottage, pets, private, convenient, parking

This secluded mid century cottage is just minutes to downtown and other amenities. Located in Clifton Heights, this three bedroom, bath and a half home is inviting and cozy. Located 6 miles from two large malls, 1 mile from the new walking bridge over the Ohio River, and one and a half miles to unique shopping, nightlife and restaurants. Also, the home is only a short distance to I 71 and I 64. This makes everything convenient and accessible from this private location. The home has vintage charm with renovations for convenience. Each Bedroom has a flatscreen TV as well as a 56 inch flatscreen in the living room. There is a private front yard with gardens, seating, and a grill. There are 6-7 spaces for off street parking. The eat-in kitchen seats six, with a double oven microwave, full-size fridge, gas stove and a dishwasher. There is service for 12 including Louisville Hadley Pottery.

LocationFamilyCheck-in

4.98 out of 5 average rating, 128 reviews

Home in Prospect

LUX Waterside Retreat|Geo Dome+Outdoor Fire Table

✅Climate controlled GeoDome w/movie screen ✅Fire Table ✅Family+baby friendly👶 ✅Not in a Neighborhood Tucked away on two private acres along Harrods Creek, this beautifully remodeled historic home offers rare privacy, creekside charm, and easy access to Louisville's best attractions. No crowded neighborhoods - just open space, creek views, and boats drifting by. Perfect for bourbon tours, concerts, and Derby weekends, you can explore the area, then return to your own peaceful creekside retreat.

ValueLocationGetting around

The charming brick exterior of the house is complemented by large windows and a peaked roof. A well-maintained lawn features vibrant yellow daffodils in the foreground, creating a welcoming entryway framed by steps leading to the front door.

4.99 out of 5 average rating, 298 reviews

★WorldlyHighlands★LARGE Kitchen, FASTWifi, Parking

Upper Highlands home in privileged location w/ keyless entry. A block from Bardstown Road, close to I-264 for fast commutes and all the HIGHLANDS excitement. Harmony of convenience & quiet allows for perfect stays for families, couples, business/vacation travelers alike. •4 bedrooms (includes basement), and 4 SMART TVs •Large kitchen, appliances, 2019-23 •PARKING up to 4 cars •Back porch GAS GRILL •Patio furniture * FIRE PIT, added Oct-2024 •Super Fast fiber-optic WiFi •Samsung Washer&Dryer

ValueFamilyBarbecue

The open living area showcases hardwood floors and features natural light from large windows. A leather couch is positioned beside a wooden coffee table. The modern kitchen includes a spacious island with bar seating for six, complemented by white cabinetry and stainless steel appliances.

4.98 out of 5 average rating, 296 reviews

The Lakehouse at Progress Park in Derby City

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The Lake house combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

ValueLocationHospitality

A cozy living area features a stone fireplace with a wooden mantel, complemented by a modern television mounted above. An acoustic guitar is positioned next to a comfortable armchair, with light streaming through sheer curtains over large windows, illuminating the space.

4.98 out of 5 average rating, 133 reviews

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!

FamilyLocationAccess

The exterior of a charming single-story house is shown, featuring a covered porch and stone columns. Lush green bushes frame the entrance, and two seats are visible on the porch. A modest yard surrounds the house, with a clear sky above.

4.9 out of 5 average rating, 345 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

LocationFamilyNearby

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.

4.88 out of 5 average rating, 242 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.

FamilyValueComfort

A fenced backyard features a circular stone fire pit surrounded by four Adirondack chairs. A hammock hangs invitingly between two trees, with string lights softly illuminating the area. The lush grass complements the warm ambiance created as the sun sets in the background.

4.96 out of 5 average rating, 186 reviews

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Michael and Ashley (Lumos Stays) welcome you to Louisville, home of bourbon! Centrally located, minutes from the interstate, and close to downtown and the bourbon trail, this is your home base for adventure. Enjoy the 65" 4K Roku TV, fast wifi (~317mbps), green tea memory foam mattresses, modern kitchen, kid-friendly amenities… and did you see that outdoor space? Solo Stove fire pit, hammock, propane grill, and games. Enjoy the private fenced-in backyard and large driveway!

ValueFamilyIndoor spaces

Superhost

The exterior showcases a historic building with large windows allowing natural light. A welcoming entrance leads to additional outdoor seating. An indoor game area features a shuffleboard table and playful décor. A cozy outdoor space is highlighted by a fire pit, surrounded by modern seating.

4.92 out of 5 average rating, 296 reviews

Best Location in the City-2 Story Patio & Hot Tub

The Saddle Inn has everything you need for your upcoming stay. Situated in the heart of the city and walking distance to the best restaurants and bars in town, you are booking convenience when you book our home. This house has vintage Kentucky flare with modern furnishings & updates. It boasts 3 bedrooms, a 2 story patio, hot tub, fire pit, ping-pong table, shuffleboard, and all the bourbon barrels one can hope for in Kentucky. There's no better location than this one.

FamilyLocationHospitality

A comfortable living area features a light grey sofa and two matching armchairs, arranged around a circular coffee table on a textured area rug. A ceiling fan hangs above, and natural light filters through the large window, illuminating black and white framed photographs on the walls.

5.0 out of 5 average rating, 146 reviews

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

FamilyValueBarbecue

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.

4.98 out of 5 average rating, 210 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!

FamilyLocationKitchen

4.93 out of 5 average rating, 199 reviews

A spacious living area is equipped with a large sectional sofa and a wooden coffee table, providing a comfortable gathering space. The modern kitchen features stainless steel appliances and dark cabinetry, while an open layout invites natural light from the adjacent windows.

Home in Germantown

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.

LocationFamilyCheckout

Popular amenities for St Matthews house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 130 reviews

An inviting open kitchen showcases modern appliances and a spacious countertop, perfect for meal preparation. A cozy living room features a plush sofa, complemented by natural light from nearby windows and tasteful decor that enhances the comfort of the space.

Home in Prospect

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

FamilyLocationPool

4.93 out of 5 average rating, 106 reviews

An outdoor space features a large swim spa hot tub beside a wooden bar with four stools. A gazebo is adorned with seating for relaxation. A stone pathway leads towards the backyard, with a manicured lawn and trees bordering the property.

Home in Clarksville

10 min to Lou~Huge Hot Tub~Fenced Backyard~Games

FamilyLocationLaundry

A comfortable living area is furnished with a leather recliner and a wooden coffee table. A television is mounted on the wall opposite the open kitchen, where light cabinetry and seating at the counter are visible. Natural light enters the room, creating a warm ambiance.

4.95 out of 5 average rating, 113 reviews

Cozy Neighborhood Home - 10 min to Louisville!

ValueLocationCheckout

4.97 out of 5 average rating, 275 reviews

6 Kings + Hot Tub | Near Expo, Track & Downtown

FamilyValueParks

A split-level home is displayed, featuring a combination of brick and siding. A well-maintained garden with vibrant flowers lines the front. A mature tree provides shade, and the house is accented with dark shutters beside the windows. A welcoming sign is visible in the yard.

4.94 out of 5 average rating, 36 reviews

The Getaway!

FamilyLocationIndoor spaces

4.94 out of 5 average rating, 18 reviews

Romantic Waterfront View Games HotTub Theater Pool

FamilyLocationAccess

4.99 out of 5 average rating, 69 reviews

A colorful living area features a striking red ceiling and vibrant wall art depicting a circus theme. Seating includes a gray sofa, a round dining table, and unique patterned chairs. Large windows allow natural light to fill the space, enhancing the playful decor.

Home in Prospect

CIRCO LOCO - uNCommon Stay

FamilyValueAccuracy

Superhost

4.58 out of 5 average rating, 48 reviews

Entire Home with Indoor Spa & Pool

LocationFamilyCondition

Weekly house rentals

A bright living room features a dark tufted sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, and a large flat-screen TV is mounted above a white mantel. Two armchairs are positioned near a window, with natural light flowing into the space.

4.94 out of 5 average rating, 461 reviews

DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT

FamilyLocationQuiet

The exterior view of the red-themed house is shown, emphasizing the sloped roof and welcoming front porch. A spacious deck features seating options and a grill. Lush greenery surrounds the area, contributing to a peaceful outdoor environment.

4.99 out of 5 average rating, 122 reviews

Colonial Hideout | Close to fairgrounds!

FamilyValueSleep quality

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.

4.96 out of 5 average rating, 180 reviews

The River's Edge Oasis, close to downtown

FamilyValueWalkability

A waterfront home is set against a backdrop of blue skies and trees. The structure features a red exterior with multiple levels, large glass doors, and a spacious deck supported by wooden beams. A green lawn surrounds the building, enhancing the outdoor space.

4.96 out of 5 average rating, 113 reviews

Waterfront Red Ruby ping pong shuffle board

FamilyLocationOutdoor spaces

The exterior of the home features a front porch with steps leading to the entrance. A small table and chairs are positioned on the porch, surrounded by greenery. The yard is open with a gravel driveway and additional foliage visible along the perimeter.

4.96 out of 5 average rating, 343 reviews

Thompson Hideaway

LocationValueParks

4.95 out of 5 average rating, 110 reviews

Luxury 2-Story Clifton Duplex | 2 KingBeds (Unit2)

LocationFamilyWi-Fi

A charming brick exterior of a single-story home is framed by a lush green lawn. The front porch is furnished with a white railing and features a small potted plant at the entrance. A wooden fence provides privacy in the background.

4.93 out of 5 average rating, 152 reviews

Derby Dreaming in the Julep House - Churchill/Expo

ValueFamilyLayout

A cozy living space features a brown sectional sofa adorned with a cushion displaying the phrase 'CALL ME OLD FASHIONED.' Green plants are positioned beside the couch, while patterned wall art and a decorative sign contribute to the inviting decor.

4.99 out of 5 average rating, 256 reviews

"Call Me Old-Fashioned"in Derby & Bourbon Country!

FamilyLocationBreakfast

Private house rentals

5.0 out of 5 average rating, 79 reviews

Groovy Hidden Gem w/Park 2 min Walk

ValueLocationKitchen

4.95 out of 5 average rating, 85 reviews

OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck

ValueLocationNearby

The living area is styled with wooden beams and a stone accent wall featuring a mounted TV. A cozy couch is paired with a draped blanket, while a dining table is positioned nearby, illuminated by natural light from large windows.

5.0 out of 5 average rating, 52 reviews

The Cottage @ Mellwood

LocationFamilyHot tub

A cozy living area features a spacious sectional sofa adorned with various decorative pillows. Two antique-style chairs are positioned nearby, and warm light is provided by a standing lamp. The room is enhanced by rich red curtains and a patterned area rug, creating a comfortable ambiance.

4.98 out of 5 average rating, 50 reviews

Swanky, Retro, Artist's Home, St Matthews, KY.

LocationFamilyParks

Superhost

4.85 out of 5 average rating, 71 reviews

Spacious home near Churchill Downs for Derby

FamilyLocationAccess

An open living space is showcased, featuring a black sofa and a light-colored coffee table. A large island with a marble countertop is visible, surrounded by pendant lighting. A dining table is set, with decorative elements like a tray containing stones and dried plants.

4.97 out of 5 average rating, 88 reviews

Radiant Louisville Getaway

FamilyValueGetting around

The exterior of a single-story home is showcased, featuring a stone façade and dark shutters. A well-maintained lawn with green grass surrounds vibrant pink flowers. A concrete walkway leads to the front door, while parked cars illustrate the neighborhood setting.

5.0 out of 5 average rating, 18 reviews

Charming House in the Heart of St. Matthews

LocationFamilyHospitality

A living area features dark blue walls enhanced by natural light from multiple windows. A gray sofa with decorative pillows faces a wall-mounted television. A coffee table and side tables add functionality, while a dining table with teal chairs occupies one corner. Plants provide a touch of greenery.