Vacation rentals with outdoor seating in St. Matthews

4.95 out of 5 average rating, 347 reviews

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

4.99 out of 5 average rating, 240 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.

4.98 out of 5 average rating, 101 reviews

Home in Crescent Hill

3 bedroom Crescent Hill cottage

Located on a wide, tree-lined avenue, this comfortable, stylish, and well-appointed Dutch Colonial is only a few minutes drive from Louisville's most popular entertainment districts, restaurants, and boutique shops along Frankfort Ave, Bardstown Rd, NULU and Downtown. Guests will enjoy the surroundings of one of Louisville's most desirable neighborhoods with Whitehall and Boyce College within walking distance and Garden Court, as well as historic Cherokee Park just a short drive away!

4.91 out of 5 average rating, 284 reviews

Home in Clifton Heights

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.

4.87 out of 5 average rating, 217 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.

4.96 out of 5 average rating, 236 reviews

502 House @ Progress Park w/ Game Room

Welcome to Progress Park! A true getaway for fun! Located on a 12 acre Airstream Glamping resort w/ a 2 acre swimming pond. Sleeps 8 comfortably in the beds with 2 leather futons. Enjoy all the luxuries of home w/ added amenities such as a custom game room & luxurious backyard with TV, firepit & grill. Relax, unplug and reconnect in our little slice of heaven. Progress Park has 8 total units on site. 2 houses, 5 airstreams & a bunk house. *DERBY IS A MIN THURS-SUN REQUIRED

4.98 out of 5 average rating, 264 reviews

Fall Haven - King Beds, 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*

4.82 out of 5 average rating, 118 reviews

Home in Clifton

Eclectic/Modern 1 BR in Clifton!

Updated 1 bedroom/1 bathroom stylish retreat right in the heart of the Historic Clifton neighborhood. Clifton is directly off Frankfort Avenue near the Highlands, Nulu, St Mathews, and Old Louisville neighborhoods. This 600 sq ft charming shotgun home was built in the 1900’s and it has a ton of character and “old home” charm, while still having updated features throughout. This home is very close to many restaurants and shops! You can walk, drive, or bike to Frankfort Ave.

4.97 out of 5 average rating, 133 reviews

Guesthouse in Louisville

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.)

4.98 out of 5 average rating, 139 reviews

Apartment in Louisville

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

Guest suite in Louisville

4.99 out of 5 average rating, 208 reviews

Olive Branch Suite with projector screen in E Lou

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. We also provide a fold out desk that guests can use for a remote work space if desired.