Holiday rentals in Saint Matthews

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.

4.94 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, 209 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, 247 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*

Guest house in Louisville

4.91 out of 5 average rating, 545 reviews

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, 164 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.

Superhost

4.78 out of 5 average rating, 199 reviews

20-2 Queen Beds-1 Bath-Pet Friendly-1st Floor

Frankfort Ave B&B Unit 20. This is a 2 bedroom 1 bath 1st floor suite that allows your family to relax in the comforts of a wonderful peaceful apartment. Complex comes with a dog park so you can travel with your pet. We are close to everything. YUM Center 2.8 miles Lynn Stadium 1.8 miles Downtown Convention Center 1.7 miles State Fair Grounds 2.9 miles Headliners 1.2 miles Mercury Ballroom 1.3 miles Center for the Arts 1.6 miles

4.95 out of 5 average rating, 326 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.

Guest house in Louisville

4.9 out of 5 average rating, 115 reviews

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.

Guest house in Louisville

4.93 out of 5 average rating, 1,009 reviews

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, 200 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!

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Popular amenities for Saint Matthews holiday rentals

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Other great holiday rentals in Saint Matthews

4.95 out of 5 average rating, 130 reviews

Highlands Zen Oasis • Comfy, Clean & Cozy

KimberlyRating, 5 stars2 weeks ago

Melody’s place is calm, peaceful and a comfortable setting. She has thought of every detail and is proactive with instructions and sights that are around the area. Worked out perfectly for my visit!

Apartment in Saint Matthews

4.9 out of 5 average rating, 30 reviews

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.

4.92 out of 5 average rating, 79 reviews

The Dream Location of Louisville

WendyRating, 5 stars1 month ago

We stayed here for 2 nights and enjoyed it very much! very clean, comfy beds, plenty of room, love the extra snacks provided and toiletries in the bathroom in case you left something behind! definitely will stay again when we come back next year!

Apartment in Crescent Hill

4.96 out of 5 average rating, 142 reviews

Hidden GEM, newly furnished in a safe, great area

CamRating, 5 stars3 weeks ago

Karen’s place was great! Very clean and had everything we would need. Very cute and comfortable. Would definitely stay again!

4.9 out of 5 average rating, 475 reviews

Your Cozy Louisville Hideaway in the Highlands

JessicaRating, 5 stars3 weeks ago

The home was beautiful and exactly as listed!! The beds were very comfortable and the shower pressure was sublime. I would absolutely stay again!!

Superhost

Loft in Louisville

4.87 out of 5 average rating, 30 reviews

Cottage in the city

JessicaRating, 5 stars2 weeks ago

Beautiful place located on a quiet side road in the midst of nature. The bed was very comfortable and we felt right at home.

4.96 out of 5 average rating, 303 reviews

Seneca View

ElaineRating, 5 stars3 weeks ago

The apartment at Gregory's place was well appointed with all needed for convenience and comfort. It is in a lovely, established neighborhood, yet not too far from restaurants and easy access from I-64. I would highly recommend it.

Superhost