Vacation rentals in Saint Matthews

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Top-rated vacation rentals in Saint Matthews

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 151 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Jan. 1 – 8

$235 CAD per night

Guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 105 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Mar. 2 – 9

$151 CAD per night

Guest favourite

Townhouse in Louisville

4.95 out of 5 average rating, 211 reviews

Louisville Charm: Walk to it All! Central & Quaint

Welcome to the charm and character of Louisville! WALKING DISTANCE to everything you can enjoy. You will be right off the main strip of Frankfort Ave near Nulu. Less than a 5min walk to local breweries, coffee shops, restaurants, bars +more! Your experience includes: -queen suite -clawfoot tub shower combo -rollaway twin bed -stocked kitchen w/blender & toaster -AT&T fiber wifi -wine fridge -smart tv -desk workstation -Levoit air purifier -coffee & tea -happy live plants -inviting neighborhood

Sep. 4 – 11

$218 CAD per night

Guest favourite

Apartment in Saint Matthews

5.0 out of 5 average rating, 77 reviews

Swanky Fully Equipped St. Matthews Apartment

Swanky East End Private Apartment. Completely renovated in 2018. New Shower, fully equipped kitchen. Huge walk in closest, FlatScreen TV and WIFI all included. Party Deck and Spaceous Living Room are ready for your Visit. King Bed and Queen Sleeper Sofa with spacious living, await up to 4 guests. Great venue for Trinity Football, University of Louisville Sporting events, Churchill Downs, or simply hitting the Bourbon Trail. 10 min. Uber to Whiskey Row and Distillery And/or and Nulu District

Jan. 16 – 23

$189 CAD per night

Guest favourite

Guest suite in Louisville

4.93 out of 5 average rating, 209 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.

Nov. 5 – 12

$129 CAD per night

Guest favourite

Apartment in Louisville

4.98 out of 5 average rating, 248 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Oct. 6 – 13

$183 CAD per night

Guest favourite

Home in Louisville

4.85 out of 5 average rating, 164 reviews

Private EAST END gem, minutes from 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.

Jun. 21 – 28

$141 CAD per night

Guest favourite

Guesthouse in Louisville

4.91 out of 5 average rating, 450 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/

Aug. 18 – 25

$109 CAD per night

Guest favourite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Sep. 6 – 13

$216 CAD per night

Guest favourite

Guest suite in Louisville

4.95 out of 5 average rating, 288 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.

Jan. 16 – 23

$149 CAD per night

Guest favourite

Guesthouse in Louisville

4.93 out of 5 average rating, 785 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 front of the garage. Pets are welcome, plz add them when booking.

Jun. 3 – 10

$141 CAD per night

Guest favourite

Guest suite in Louisville

4.99 out of 5 average rating, 153 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.

Jul. 2 – 9

$145 CAD per night