Holiday rentals in Saint Matthews

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Top-rated holiday rentals in Saint Matthews

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Guest favourite

Flat in Louisville

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.

Top guest favourite

Guest suite in Louisville

4.94 out of 5 average rating, 277 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.

Top guest favourite

Cabin in Louisville

5 out of 5 average rating, 213 reviews

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.

Top guest favourite

Home in Louisville

4.99 out of 5 average rating, 249 reviews

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 favourite

Guest house in Louisville

4.91 out of 5 average rating, 546 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/

Top guest favourite

Flat in Louisville

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.

Superhost

Flat in Louisville

4.78 out of 5 average rating, 203 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

Top guest favourite

Guest suite in Louisville

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.

Guest favourite

Guest house in Louisville

4.91 out of 5 average rating, 117 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.

Top guest favourite

Guest house in Louisville

4.93 out of 5 average rating, 1,013 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.

Top guest favourite

Guest suite in Louisville

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.

Top guest favourite

Flat 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.