Vacation rentals in Saint Matthews

A modern kitchen features dark cabinetry and a large island with seating for two. Natural light pours in through a window, illuminating the white subway tile backsplash and stainless steel appliances. Wooden ceiling beams add character to the airy space.

4.94 out of 5 average rating, 286 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.

An inviting outdoor space features a stone fire pit surrounded by several colorful seating options. Various patterned chairs and stools are arranged on a stone patio, with greenery providing a natural backdrop. A wooden table adds to the cozy ambiance of this fenced-in yard.

4.94 out of 5 average rating, 278 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, 213 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.

4.99 out of 5 average rating, 249 reviews

A wooden bridge extends over a lush green path, surrounded by vibrant trees and dense foliage. Sunlight filters through the leaves, creating a serene atmosphere. The bridge features metal railings, adding a modern touch to the tranquil natural setting.

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, 547 reviews

Guesthouse in Louisville

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, 168 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.

4.96 out of 5 average rating, 303 reviews

Seneca View

Open, airy space with modern amenities. Plz, NO smoking, toking , vaping, or any drug use in/on property-- $300 fine. Convenient location in a quiet, sought-after neighborhood, yet within a few minutes of a bustling, busy Bardstown Road with lots of places to eat, shop and browse. Easy access from all major interstates: I-71, I-65 and I-64. Come stay for a week on business (work desk is set up) or use for a fun, getaway weekend.

A cozy seating area features a daybed with colorful cushions and a contrasting metal chair. A gas fireplace is positioned beside a television, which is mounted above a decorative stone surround. Vintage decor elements, including signs and lamps, enhance the inviting space.

4.95 out of 5 average rating, 327 reviews

Highlands Lower Level Studio Guest Suite

Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.

4.91 out of 5 average rating, 117 reviews

A pinball machine stands against a gray wall, adorned with colorful graphics. A cozy gray sectional couch is positioned nearby, complemented by a small yellow table. Natural light filters through a window, enhancing the inviting atmosphere of the entertainment space.

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, 1,013 reviews

A blue carriage house is presented, featuring a spacious driveway with a two-car garage below. A staircase leads to the upper level, framed by a tree dusted with snow, creating a serene winter scene.

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.

Two remote controls are placed on a wooden table. One is a Roku remote with colorful buttons for various streaming services, while the other is a Vankyo remote with a simpler design, featuring an array of buttons for navigation and control.

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.

4.85 out of 5 average rating, 131 reviews

A modern bathroom sink is featured with a round mirror above and a towel hanging on a ring nearby. A decorative dispenser holds liquid soap, while a toilet paper roll is positioned beneath. The decor exhibits a clean and organized appearance.

Apartment in New Albany

1 bedroom efficiency kitchenette

Studio apartment is unique and inviting. Plan a mini breakaway in this private basement retreat. New 55” TV with Netflix access or perhaps a Rip Van Winkle rest on the Queen size bed (hmmmmm so comfortable). Love to cuddle under airy light soft comforter & blankets. Walk, or drive, to stores & restaurants about 5/6 blocks away.

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Popular amenities for Saint Matthews vacation rentals

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Other great vacation rentals in Saint Matthews

4.83 out of 5 average rating, 6 reviews

Cozy Louisville Apt w/ Parking|Great Location!

CristianRating, 5 stars2 weeks ago

Great host, great apartment to be honest, great location, everything is close and I’ll be waiting to be here again.

4.99 out of 5 average rating, 149 reviews

The spacious basement living area features a large sectional couch and a cozy curved seating arrangement, providing ample space for relaxation. A screen is positioned at one end, suitable for movie viewing. Soft lighting enhances the inviting atmosphere of the room.

Home in Louisville

"The Brook" - Louisville

JulieRating, 5 stars6 days ago

Comfortable home in great neighbourhood. Had everything we needed for our stay. Close to everything. Good communication from Jordan.

5 out of 5 average rating, 29 reviews

A classic hammock is seen suspended between two trees, providing a relaxing spot. It features a decorative pillow with a blue and white pattern, resting on a woven surface. Lush greenery and a wooden fence create a serene outdoor setting.

Home in Crescent Hill

Little Gem off Frankfort Ave

JonRating, 5 stars2 weeks ago

Exceptionally clean, quiet, and professional. Thanks!

A modern bathroom features a glass shower with a rainfall showerhead and built-in shelves. A compact vanity with a mirror and a countertop sink is present. Soft blue walls and white tiles enhance the bright ambiance, while a gray bath mat lies on the floor.

4.97 out of 5 average rating, 131 reviews

Buechel Beauty

Erik & MelissaRating, 5 stars1 month ago

Kristin’s place is so cute! She let us know ahead of time that the weather was supposed to get bad during our stay, and that we would be able to take shelter with her and her family. Thankfully the weather didn’t get too bad. But her kindness and communication were top notch!

4.9 out of 5 average rating, 30 reviews

A power surge protector with multiple outlets and USB ports is mounted on the wall. A red indicator light is illuminated, signifying active power delivery. The surrounding wall is neutral-colored, contributing to a clean and organized appearance.

Condo in Saint Matthews

Chateau St. Matthews: Style & Quiet 1B Condo

TiffanyRating, 5 stars1 month ago

We had a wonderful stay at Patrice's place! The apartment was incredibly clean and well-equipped and the location was close enough for exploring the city. Patrice was also extremely responsive and helpful, always going above and beyond to ensure our comfort and offering assistance in any way. I highly recommend! Pleasant experience. The location of the condo was near to many of the places we wanted to visit. It was about a 10 min Uber ride to the Downtown District during Kentucky Derby weekend. It was about a 15 to 20 min ride to Churchill Downs.

Guesthouse in Crescent Hill

A modern guesthouse exterior is framed by lush trees, showcasing a blend of reclaimed wood. Stairs lead to a welcoming entrance, complemented by large windows that provide natural light. The building features a two-car garage below, with a clean concrete driveway.

5 out of 5 average rating, 60 reviews

New custom guesthouse | Free parking | Sleeps 4

CarrieRating, 5 stars1 week ago

I had a great stay during a long work week and it was the perfect environment to focus while also being close to walkable shops and local restaurants. Stylish custom build with beautiful antique furniture too. Friendly hosts and a wonderful stay!

A bottle of Angel's Envy Finished Rye whiskey is displayed alongside a tasting glass filled with amber liquid. The sun shines brightly in a clear blue sky, casting a warm light on the bottle, which is set on a wooden surface. A cork is placed nearby.

4.93 out of 5 average rating, 81 reviews

The Dream Location of Louisville

KorrieRating, 5 stars6 days ago

The hosts were helpful and responsive. Both answered any questions. Lots of things to do to walk to. The hosts offered snacks and mini bats and horseshoes for the kids. Very beautiful space with lots of games for the kids to play too.