Holiday houses in Saint Matthews

Apartment in Cherokee Triangle

4.94 out of 5 average rating, 285 reviews

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.

4.9 out of 5 average rating, 475 reviews

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!

4.94 out of 5 average rating, 276 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, 212 reviews

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.

4.99 out of 5 average rating, 248 reviews

Home in Louisville

NEW Hot Tub, Walk 2 Park, Whole Foods, Movies Mall

* 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*

4.91 out of 5 average rating, 545 reviews

Guesthouse in Clifton

Cute Carriage House off Frankfort Avenue

Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/

4.98 out of 5 average rating, 166 reviews

Dome in Mount Washington

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.

4.91 out of 5 average rating, 116 reviews

Guesthouse in Louisville

Prime Location, Private, games, pinball Fun!"

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.

4.93 out of 5 average rating, 1,010 reviews

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.

4.99 out of 5 average rating, 201 reviews

Olive Branch Suite in East Louisville Neighborhood

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.

4.97 out of 5 average rating, 130 reviews

Buechel Beauty

The 'Buechel Beauty' is centrally located with almost all of Louisville accessible within a 15 minute drive. Looking for somewhere to eat while you're here? You're in luck -- Bardstown Road and all its wonderful restaurants is just minutes way or take a trip around the world with many international restaurants right around the corner!

Apartment in Saint Matthews

4.97 out of 5 average rating, 116 reviews

cozy two bedroom apartment

Newly styled 2 bed/2bath apartment in St. Matthews. This second floor unit has lots of natural light, hardwood floors throughout, and is located in a quiet neighborhood within 10-15 minutes to Frankfort Avenue and downtown Louisville. This apartment is also a very close drive to many shops, local restaurants, and bars.

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Other great holiday rentals in Saint Matthews

5 out of 5 average rating, 41 reviews

Home in Louisville

Luxe Lyndon Home < 11 Mi to Dtwn Louisville!

LynnRating, 5 stars1 week ago

I really enjoyed this place. I've stayed in a lot of places and this one was one of my favorites by far. Super clean and great amenities and a really well stocked kitchen for cooking. I enjoyed the back porch coffee time every morning too!

4.85 out of 5 average rating, 249 reviews

Apartment in Louisville

The Nest

Kerry XuRating, 5 stars1 week ago

We stopped at Louisville for a road trip. Sarah’s place was clean and well organized. We had a great experience there!

Apartment in Crescent Hill

4.99 out of 5 average rating, 176 reviews

Urban Bourbon Farm Loft

MatthewRating, 5 stars2 days ago

It was a great place, has everything you need!

Guest suite in Windy Hills

4.95 out of 5 average rating, 55 reviews

Comfy Getaway Guest Suite in Louisville

AndreaRating, 5 stars3 weeks ago

Keith and Angela’s place was the perfect place to stay while visiting my parents in Louisville. We were walking distance from my parents and really enjoyed being close to the restaurants in Holiday Manor. The hosts were super responsive when we had questions about parking and controlling the AC when we got a little chilly. The apartment was spacious and comfortable and we can’t wait to stay there again the next time we’re in town!

4.98 out of 5 average rating, 43 reviews

Home in Louisville

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

NatashaRating, 5 stars1 month ago

Despite the rainy Derby weekend, our stay at James's Louisville home was absolutely PERFECT! The central location made it easy to get to all the Derby festivities while giving us a warm, dry haven to return to after the races. The eclectic artwork throughout the house created such a unique atmosphere - each room offered something new to discover and appreciate. James was an exceptional host - responsive, attentive, and went above and beyond to accommodate our needs. This gem in Louisville turned our rainy Derby weekend into a memorable experience. Thank you James!

Guesthouse in Louisville

4.85 out of 5 average rating, 26 reviews

Chic Louisville Carriage Apt - Game Room -Sleeps 4

TonyRating, 5 stars1 month ago

This was the place I needed for the weekend. It was very Peaceful and the place was so nice, clean and relaxing! Maria was so nice and very easy to communicate with. I would recommend this place to everyone.

5 out of 5 average rating, 19 reviews

Home in Clifton Heights

Bourbon City Bungalow

LynneRating, 5 stars1 day ago

The house was perfect for two people, clean super cute decor. The location is close to everything, and Daniel’s guide book had great recommendations. We appreciated how easy Daniel was to communicate with. We will definitely use this as our go to while in Louisville!