House vacation rentals in Shelbyville

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Popular amenities for Shelbyville house rentals

House rentals with a pool

Guest favorite
A sparkling pool is surrounded by a stone patio and six lounge chairs, inviting relaxation. Umbrella shade provides a resting area, while string lights illuminate the scene as dusk sets in. Lush trees add a natural backdrop, enhancing the tranquil outdoor atmosphere.
Home in Shelbyville
4.97 out of 5 average rating, 29 reviews

Pool is Open! + Hot Tub, 10 min to Bulleit

AngelaRating, 5 stars6 days ago
We had a wonderful stay. The family loved to pool and hot tub. We were close to many activities. Jill did an excellent job communicating with me and answering all my questions. We are looking forward to booking our next stay.
Guest favorite
The exterior of a two-story colonial home is displayed, featuring a red brick facade, white columns, and green shutters. A spacious lawn surrounds the house, complemented by well-maintained landscaping, with a screened porch visible on the right side and a tree to the left.
Home in Shelbyville
4.94 out of 5 average rating, 70 reviews

B on the Bourbon Trail with pub, pool and hot tub

DanRating, 5 stars1 week ago
Had a excellent time at this location. The house was beautiful with great amenities including an amazing bar! Great location for visiting distilleries or Churchill Downs.
Top guest favorite
A bright and inviting outdoor area features a refreshing swimming pool with clear blue water. Surrounding the pool are sun loungers and a shaded gazebo, set against a backdrop of lush trees and well-maintained landscaping.
Home in Lexington
4.97 out of 5 average rating, 115 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

GeorgeRating, 5 stars3 weeks ago
Harrison was an amazing Host! The house was immaculate and had everything you could want to feel at home and relax. This is a premier spot to take your family for Visiting the gorgeous and historic Lexington. Thank you so much for an amazing place to gather as we celebrated our son’s graduation.
Top guest favorite
Home in Prospect
5 out of 5 average rating, 107 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

BetsieRating, 5 stars2 weeks ago
Amazing stay. Nicole was super responsive and over the top helpful with info and recommendations. The house was beautiful. Everything exceeded our expectations. Looking forward to coming back !
Top guest favorite
A spacious, single-story house features a clean white exterior with dark roofing and large arched windows. Manicured grass surrounds a central pathway that leads to the front door, framed by evenly spaced shrubs. A clear blue sky adds to the welcoming atmosphere.
Home in Bagdad
5 out of 5 average rating, 30 reviews

Private Estate on Bourbon Trail w/ Beautiful Pool

MeredithRating, 5 stars1 week ago
We had four adults and three kids staying at David’s place and it was great! It’s even better than the pictures. We loved the beautiful rural setting, yet also appreciated it was only 10 min from grocery stores and shopping. The pool and in home movie theater were big hits with our family. We grilled often and cooked in the kitchen, which had everything we needed. We appreciated all the space to spread out as well as the numerous areas to gather and play. We’d definitely stay here again!
Top guest favorite
A refreshing pool is surrounded by a wooden deck, featuring lounge chairs and a table with an umbrella. Floating toys are visible in the clear water, while lush greenery and trees provide a natural backdrop to the inviting outdoor space.
Home in Lexington
5 out of 5 average rating, 102 reviews

Game room! 5 beds an 4 bedrooms

StephanieRating, 5 stars1 week ago
This place was very nice and Jeff was a terrific host! Perfect for a nice family getaway. Close to everything. If you are looking for fun and relaxation, this is the house. Game room was a huge bonus with 2 arcade games and several board games. The backyard is so cute, private and cozy. Kitchen was stocked with coffee and everything you need and the beds were comfy. This is a must stay. Very cute house! Loved it!
Guest favorite
A comfortable living room is presented with deep blue walls and large windows, allowing natural light to fill the space. Two sofas and several accent chairs are arranged around a wooden coffee table, with decorative pillows adding color. Vibrant artwork adorns the walls.
Home in Louisville
4.98 out of 5 average rating, 162 reviews

KY Derby, Bardstown Road, Brewery, 2Decks w Porch

EmileeRating, 5 stars3 weeks ago
Louisville exceeded our expectations and so did this home! Extremely spacious and well stocked for four adults and kids under 8. Lots of bathrooms and the beds were super comfy. Huge yard too! We’d definitely stay again!!
Superhost
A dual-level deck houses an above-ground swimming pool with clear blue water. Two custom wooden chairs provide seating near the pool's edge, framed by a brown fence and lush greenery in the background. The deck surface is finished in light grey, enhancing the outdoor space.
Home in Lawrenceburg
4.81 out of 5 average rating, 165 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

JoshRating, 5 stars7 months ago
Overall great stay ! Exactly as described from the hot tub down to the amenities in the house. Very peaceful area and very easy to get to many area attractions! Thank you Joe !

Weekly house rentals

Guest favorite
A single-story home is surrounded by a snowy landscape, highlighting the property's spacious front yard. Sunlight casts shadows from nearby trees onto the ground. The home features a covered porch with wooden columns, providing a welcoming entrance.
Home in Simpsonville
4.91 out of 5 average rating, 11 reviews

Eastern Sky

ChloeRating, 5 stars2 weeks ago
We were in town for the Kentucky Ren Faire and it was a great location! Beautiful and peaceful location.
Top guest favorite
A panoramic view reveals lush greenery along Guist Creek Lake, with gentle contours of the landscape reflected in the water. The image captures a spacious deck equipped with seating, creating a serene spot for relaxation and observation of the natural beauty.
Home in Shelbyville
5 out of 5 average rating, 27 reviews

Bourbon by the Lake

DarrellRating, 5 stars1 month ago
The location is superb is you are trying to see Kentucky. The distance to Louisville, Lexington and Frankfort are all about equal. Shelbyville is a few miles away and it has some great restaurants and nice shopping. While staying there we visited Churchill Downs, Buffalo Trace and Shelbyville. The house has kayaks and a little fishing equipment. We spend a lot of time on the decks and fishing on the dock. This was a great, peaceful getaway from life at home.
Superhost
Home in Versailles
5 out of 5 average rating, 5 reviews

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

VirginiaRating, 5 stars4 days ago
The house was gorgeous and had more than enough room for the nine of us. One of the most comfortable/clean places we have stayed and have no complaints!
Top guest favorite
The entryway features a grand chandelier above a wooden staircase, framed by elegant woodwork. To the left, a spacious living area can be seen, furnished with a large sectional sofa. A decorative rug lies on the polished wooden floor.
Home in Shelbyville
5 out of 5 average rating, 37 reviews

Historic Downtown~Heart of Bourbon Trail

RebeccaRating, 5 stars2 weeks ago
Stayed at the Washington Belle for my wedding weekend and it was perfect! Myself and my bridesmaids got ready there and there was plenty of space, light, and rooms to get ready in! Everywhere is decorated so cute and the house is perfectly situated to the Shelbyville Conference Center and the downtown Main Street. We loved staying there and the host is so nice! Such a charming house!
Guest favorite
The modern kitchen features white cabinetry with sleek hardware, stainless steel appliances, and a center island. Pendant lights hang above the island, illuminating the open space. Natural light filters in from nearby windows, enhancing the inviting atmosphere.
Home in Shelbyville
4.93 out of 5 average rating, 14 reviews

Shelbyville, KY - Bourbon Trail and Horse Country.

KerstinRating, 5 stars2 weeks ago
We enjoyed the spacious home with plenty of indoor and outdoor space to relax. The linens, bathrooms, and kitchen were very clean. We appreciated that the home is pet friendly and it was easy to walk our small dogs around the neighborhood. Angus was very responsive to our booking and request. We would stay here again and conveniently located near Shelbyville Country Club.
Top guest favorite
A spacious fire pit area features comfortable Adirondack chairs arranged around a stone fire pit, surrounded by a gravel patio. String lights overhead create a warm atmosphere against the backdrop of rolling hills and a sunset sky.
Home in Bagdad
5 out of 5 average rating, 87 reviews

LUX | HotTub | Firepit | Man Cave | On BRBN Trail!

AmyRating, 5 stars1 week ago
The house looks exactly like the photos. We hung out in the garage every night and had a blast. There was plenty of room for our group of 10 in there and plenty of activities to entertain us all. There are TVs in 3 of the bedrooms and 3 community spaces, so people also have the option of doing their own thing if they prefer. The bedrooms are spacious with huge closets. I like being able to unpack and put all my luggage away when I travel, so this was amazing. We had everything we needed in the kitchen, which was also nice. The house is located just down the road from Bulleit Distillery and about 25 minutes from Buffalo Trace, which is our favorite distillery, so that worked out great. From there, we could get to any distillery we were interested in visiting in about 45 minutes or less. The host of the property was fantastic to work with and was very responsive. I really appreciated their attention to detail and customer service. I highly recommend this home!
Top guest favorite
The exterior of a single-story brick house is shown under a clear blue sky. A driveway leads to a two-car garage, and a landscaped front yard features green grass and shrubs. A large window above the entrance highlights the architectural design.
Home in Shelbyville
5 out of 5 average rating, 19 reviews

Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio

ValentinRating, 5 stars3 weeks ago
Charlie and Kate were very helpful and responsive. Their place was clean and well furnished. Must stay at if you're looking for a place in Shelbyville!
Guest favorite
A bright and spacious living area is furnished with a large sectional sofa and two comfortable armchairs. Natural light floods in through several windows adorned with light curtains. A neutral area rug anchors the seating arrangement, creating an inviting space for relaxation.
Home in Shelbyville
4.92 out of 5 average rating, 61 reviews

100 Proof Hideaway

EduardoRating, 5 stars2 weeks ago
Great home clean and well stocked. It was hard to get Ubers to get to distillery’s and back to the Airbnb.

Private house rentals

Top guest favorite
The outdoor space features a DIY pickleball court, surrounded by well-maintained grass and bordered by planters. A gazebo and hot tub are visible adjacent to the brick house, while tall trees provide a serene backdrop to the inviting courtyard area.
Home in Midway
5 out of 5 average rating, 35 reviews

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

DerekRating, 5 stars6 days ago
This house has been very well taken care of with nicely preserved midcentury details. My brothers and I really enjoyed our time there. Frankfurt is a relaxed city with amazing historical interest. We enjoyed golf, disc golf, and, of course, the local distilleries. The surrounding countryside is exactly what you would hope for in coming to Kentucky: ample rolling green hills and luxurious stables.
Top guest favorite
An aerial view captures the spacious property surrounded by lush greenery, featuring a heated saltwater pool and an inviting firepit area. The home presents a modern façade, complemented by soft evening light as the sun sets, creating a serene outdoor retreat.
Home in La Grange
4.98 out of 5 average rating, 54 reviews

Where generations come to connect | Pool | Games

KimberlyRating, 5 starstoday
Everything we hoped for and more! There are so many places to hang out and relax both inside and out. We had the perfect mix of togetherness for our party of 9, and the ability to spread out and enjoy smaller groups or solitude. Great location outside Louisville, with plenty to do in the area and nearby grocery options. The kitchen was great and the master bath was luxurious. We loved that each bedroom had king beds! Deb was incredibly responsive, flexible and helpful. Our young adults loved the converted garage (which we dubbed the man cave due to its TV, fridge, pool table and foosball table). All the fun activities in the basement were great. We would definitely stay here again!
Guest favorite
A charming cottage is positioned on a wooded ridge, featuring a welcoming front porch. Lush landscaping includes well-maintained bushes and small shrubs. Large windows provide ample natural light. The tranquil surroundings complement the serene atmosphere of the property.
Home in Taylorsville
4.92 out of 5 average rating, 24 reviews

Bourbon Trail Lake Home w/ Hot tub & King Bed

SteveRating, 5 stars1 week ago
The place was everything we wanted ton our stay. Sarah was fantastic in responding to any of our questions. I would definitely stay here again!
Superhost
A spacious living area is defined by a tall brick fireplace with a flat-screen TV mounted above. Comfortable seating includes a leather sofa, patterned armchairs, and a wooden coffee table, complemented by natural light from large windows and a warm area rug underfoot.
Home in Shelbyville
4.72 out of 5 average rating, 18 reviews

Peace and Quiet Close to Louisville - 80+ Acres

ManuelRating, 5 stars1 week ago
Everything was perfect in this house! The best Airbnb option ever that we have rented in several countries. If you are looking for a place neer Shelbyville, Louisville, etc, this is the best option that you find.
Guest favorite
A modern kitchen area displays a wooden counter with storage drawers beneath. Above, a reclaimed wood shelf houses an assortment of books and decorative items. Two mini-fridges are positioned under the counter, enhancing functionality. A potted plant adds a touch of greenery to the space.
Home in Louisville
5 out of 5 average rating, 53 reviews

Countryside Getaway

ZacharyRating, 5 stars6 months ago
We stay here every year when visiting family for thanksgiving. It is perfect for our small family. The host is always so responsive. The property is beautiful. I can’t recommend this airbnb highly enough. Thank you Gordana!!
Top guest favorite
An aerial view of the rustic country home showcases a spacious outdoor area. A round above-ground pool is situated prominently among the green lawn, surrounded by wooden decking. Nearby, several tables and a picnic space are visible, inviting relaxation and gatherings in a tranquil setting.
Home in Frankfort
4.98 out of 5 average rating, 61 reviews

MacAttie Acres

TriciaRating, 5 stars4 days ago
Well, our group of 9 had an enjoyable time in this home! It was as advertised and extremely clean, comfortable and quiet. Cindy was just the sweetest and most respectful host always available to answer questions or give recommendations. Close to great distilleries and downtown Frankfort with cute shops and dining. The pool and hot tub were clean and working and the home was well stocked with basic necessities. Highly recommended and can't wait to come back!
Top guest favorite
A charming single-story home features red brick and white siding, enhanced by festive bunting along the porch. Lush green grass surrounds the exterior, and large trees provide shade in the background, contributing to a tranquil rural setting.
Home in Pleasureville
5 out of 5 average rating, 98 reviews

Pleasureville - The name says it ALL

KalebRating, 5 stars1 month ago
Your place was absolutely amazing. The perfect old country home. The beds were super comfortable the kitchen has everything you need. The fire pit is an awesome perk to the property. I asked about going fishing and they were able to give me fantastic directions and we were able to catch some fish. I will definitely stay again when we come next year. Thank you so much for your hospitality and all your help during our trip.
Guest favorite
The living room features a mix of comfortable seating, including leather recliners and soft couches. A charming fireplace is framed by a richly patterned wall depicting horses. Natural light filters through the windows, highlighting the wooden ceiling and inviting decor.
Home in Lawrenceburg
5 out of 5 average rating, 28 reviews

Bourbon Trail! Tavern*Hot Tub * EV Charger

AmandaRating, 5 stars5 days ago
We enjoyed our stay at the Tavern. The house was very clean and the beds are comfortable. The kitchen was well stocked and had everything we needed. We enjoyed using the fire pit and hot tub after grilling steaks. The location was excellent for the bourbon trail. We were so close to everything we wanted to do.

Quick stats about house rentals in Shelbyville

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    780 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Shelby County
  5. Shelbyville
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