House holiday rentals in St. Matthews

4.99 out of 5 average rating, 194 reviews

Home in Fern Creek

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!!

4.95 out of 5 average rating, 173 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

4.91 out of 5 average rating, 281 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

4.9 out of 5 average rating, 193 reviews

Home in Highlands

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

4.87 out of 5 average rating, 215 reviews

Private EAST END gem, minutes to 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.

4.99 out of 5 average rating, 278 reviews

The Lakehouse at Progress Park in Derby City

A hidden piece of paradise on 12 acres within city limits of Louisville. The Lakehouse sits on a 2 acre pond, perfect for boating & fishing. Boats & lifejackets are provided. 3BR/1BA, sleeps 8 comfortably in the bedrooms with 2 twin murphy beds in the living room. The back yard has a covered tent & patio has a firepit & gas grill. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.99 out of 5 average rating, 259 reviews

St. Matthews Haven - Near State Fair Fun, Hot Tub

* 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*

4.98 out of 5 average rating, 122 reviews

Beautiful carriage house in Highlands Neighborhood

Newly remodeled and decorated, 2 story, 800 sq ft, 113 year old carriage house located in the highly sought Highlands neighborhood. Abundant restaurants, bars and shops are as close as 3 blocks away as well as a large grocery. Beautiful Cherokee and Seneca Park are walking distance, with hiking trails, playgrounds and tennis courts. The home is completely furnished with brand new appliances, furniture and fixtures in a contemporary and comfortable fashion.

5 out of 5 average rating, 102 reviews

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

4.99 out of 5 average rating, 162 reviews

"The Brook" - Louisville

Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!

4.97 out of 5 average rating, 241 reviews

Thompson Hideaway

Our cozy home is tucked back off the road, located directly behind the Mellwood Art Center. The neighborhood has a large selection of restaurants and one of the best bars for live music in the city Mellwood Tavern. Nulu, Downtown and the Highlands are all very close by. This home is a good option for couples, families, or a trip with friends. Great for a Travel Nurse with a dog