Vacation rentals in Pioneer Village

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Top-rated vacation rentals in Pioneer Village

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Guest favorite

A spacious great room features a comfortable sectional sofa and two patterned armchairs, arranged around a round glass coffee table. A wall-mounted television and decorative shelves are seen in the background. Natural light enters through multiple windows, illuminating the stylish decor and flooring.

Apartment in Louisville

4.97 out of 5 average rating, 62 reviews

second floor 1 bedroom + office W/D & easy parking

This duplex is nestled in the quiet and peaceful community of Zoneton. Offering the benefit of a suburb setting and only being 17 minutes away from Louisville's greatest attractions including downtown, Churchill Downs and Jim Beam Bourbon Trail. The great room boasts a full accessorized kitchen, wet bar, pull out queen sofa with memory foam & a 65" Smart TV. The bedroom has a king adjustable bed, smart TV and walk-in closet. Unit also has a dedicated office! There is Fiber optic WIFI & Netflix.

Guest favorite

A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.

Cabin in Louisville

4.95 out of 5 average rating, 344 reviews

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.

Top guest favorite

A cozy living space features a brown sectional sofa adorned with a cushion displaying the phrase 'CALL ME OLD FASHIONED.' Green plants are positioned beside the couch, while patterned wall art and a decorative sign contribute to the inviting decor.

Home in Fern Creek

4.99 out of 5 average rating, 194 reviews

"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!!

Top guest favorite

A welcoming entrance features a large covered porch supported by wooden beams. Two black and white chairs are positioned to the sides of the front door, with a small side table nearby. The lush landscaping includes neatly trimmed shrubs and a brick pathway.

Home in Shepherdsville

5 out of 5 average rating, 15 reviews

Cozy Home Near the Bourbon Trail & KY Derby

Welcome to our spacious 4-bedroom home, located between Kentucky’s iconic Bourbon Trail and all that Louisville has to offer. Just a few minutes drive to I65 close to E-town, Bardstown or Louisville. Nestled in a small, quiet neighborhood, comfortable and convenient for families, friends, or groups looking to explore the heart of Kentucky. Whether you’re here for bourbon, events, the Kentucky Derby, or relaxation, this home is your perfect getaway. Book now to make unforgettable memories!

Top guest favorite

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

5 out of 5 average rating, 234 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 favorite

An open studio apartment features a spacious layout with a wooden bed frame and a single bed. Soft light filters through multiple windows, illuminating a cozy seating area with patterned chairs and a round coffee table. Decorative elements add a touch of comfort.

Apartment in Louisville

5 out of 5 average rating, 50 reviews

Cozy Garage Apt- Country Charm with City Amenities

We invite you to enjoy city amenities in a country setting. Nestled in the heart of Fern Creek on Louisville's southeast side, our location is a convenient drive to most places with many nearby restaurants. Come leave the hustle and bustle behind as you enjoy a peaceful stay. This space is a studio apartment, one open room except for the bathroom. The apartment is located above our two car garage. You will enter through the side door. This apartment is accessed by a set of stairs.

Guest favorite

An open loft space features a spacious bed with a blue accent blanket. A comfortable sofa sits opposite a stylish dining area, adorned with a round table set for six. Large windows allow natural light to brighten the wooden flooring and inviting decor.

Loft in Louisville

4.81 out of 5 average rating, 658 reviews

DerbyLoft Louisville

Enjoy the best of Louisville in our second floor loft, a studs-up renovation with modern amenities, full kitchen, and a beautiful bathroom. We're in a central location from which guests can easily tour the heart of Louisville. Private entrance Free parking on street Free Wifi 10min (0.5mi) walk to Churchill Downs 25min (1.5mi) walk to Cardinal Stadium 5min (1.8mi) drive to historic Old Louisville 6min (1.9mi) drive to KY Expo Center 12min (3.2mi) drive to Louisville Airport

Guest favorite

The living area is furnished with a comfortable brown couch and a wooden coffee table. A flat-screen television is placed on a decorative console. A dining table with four chairs is positioned near a window adorned with sheer curtains, enhancing natural light in the space.

Home in Louisville

5 out of 5 average rating, 8 reviews

Heavenly Hillview retreat

Welcome to 423 Prairie Drive, your cozy home away from home. Just 20 minutes from downtown Louisville and its vibrant urban bourbon trail, you’re perfectly situated for adventure. Nearby Shepherdsville offers the Beam American Outpost, four award-winning wineries, the Four Roses Bourbon Warehouse and Bottling Tour, and the Gallant Fox Brewing Co. Enjoy your stay and make unforgettable memories! 3 bedrooms, 2 bath home. Available for 30 day plus stays! Brand new, book today!!

Top guest favorite

Apartment in Brooks

5 out of 5 average rating, 14 reviews

Cozy Studio in Brooks

Step in to a bright and cozy studio apartment with Moroccan flair - only 20minutes from downtown Louisville, Kentucky Kingdom and Churchill Downs, 15 minutes from the SDF airport and Bernheim Forest and 10 minutes from miles of Jefferson Memorial forest trails. Located on a country hillside with a separate entrance and a high outside deck that opens to the treetops, it's the perfect place to relax but still be close to all that Louisville has to offer.

Top guest favorite

A spacious master bedroom features a large bed with an intricately designed headboard. Accent lamps sit on each side, complemented by a beautifully patterned bedding set. A wooden dresser and a nightstand add functional elegance, while natural light enters from the window, enhancing the warm ambiance.

Guest suite in Louisville

4.96 out of 5 average rating, 327 reviews

Delectable Delor

Private section of home. There are no shared spaces, so you have privacy, but I do live on the other side of the house which is divided by a locked door. You have your own entrance through the front door, and off street parking. My entrance is the back of the house through the gate, which is off limits. Please be aware that 2 cats live on my side of the house, for those of you with allergies, but they won't have access to your space when you’re there.

Top guest favorite

An interior view of the geodesic dome features a cozy sleeping area with a king size bed and attractive bedding. A dining table with four brown chairs is positioned nearby. Natural light streams in through the large geometric windows, illuminating the earthy tones of the decor.

Dome in Mount Washington

4.98 out of 5 average rating, 185 reviews

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.

Top guest favorite

A inviting studio space features a spacious bed dressed in white linens, accompanied by a wooden nightstand. A blue sofa and a red armchair provide comfortable seating options. A flat-screen TV is positioned on a media console, enhancing the cozy atmosphere of the room.

Apartment in Mount Washington

4.95 out of 5 average rating, 205 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.