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House vacation rentals in Shelby County

Find and book unique houses on Airbnb

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Popular amenities for Shelby County house rentals

House rentals with a pool

Top guest favorite
An inviting outdoor space features a spacious in-ground pool surrounded by a decorative fence. Lush green trees provide shade, while the backdrop showcases a sunset sky with soft purple hues. Comfortable lounge chairs are positioned near the water, enhancing the area's relaxing ambiance.
Home in Mount Washington
5 out of 5 average rating, 37 reviews

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

JulianRating, 5 stars1 week ago
I have to say I had high hopes for our stay with everything in the photos, and even so my expectations were blown out of the water. It's no exaggeration to say this is my favorite airbnb I've stayed at, and the whole experience was so smooth thanks to Kaeley. The house itself is really cozy and modern, and the pool, speakeasy and the YMCA (as we called it) kept us entertained all weekend. I really couldn't recommend this stay any higher. Hoping to be back one day.
Superhost
A comfortable living area features a light-colored sectional sofa adorned with decorative cushions. A coffee table with magazines sits in the center. Above, ceiling beams and modern pendant lights enhance the open space, leading to the dining area visible in the background.
Home in Borden
4.87 out of 5 average rating, 38 reviews

Private Country Getaway 20min to Louisville w/Pool

CoreyRating, 5 stars7 months ago
This is a great place to stay, peaceful and quiet! Pool, hot tub, and bar came in handy when relaxing The margarita maker was clutch lol Dustin is always responsive when needed!
Guest favorite
A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.
Home in Midway
4.99 out of 5 average rating, 82 reviews

The Bees Wing

MadisonRating, 5 stars3 weeks ago
My group had such a great time! Looked exactly like the photos and had so much room! Everything worked great and I loved all the hot water even when we all took showers! There was lots of extras in the pantry like games seasoning cups and plates that were very helpful and a good set of condiments! Such an adorable lace and definitely would stay again next time we go to keen land! It was to cold outside for us the truly enjoy the pool but it looked lovely!
Superhost
A spacious living area features a leather sofa, a round coffee table, and hardwood flooring. An open kitchen showcases wooden cabinetry and a large island with seating. A staircase ascends to the upper level, and natural light fills the room through the windows.
Home in New Albany
4.85 out of 5 average rating, 53 reviews

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/

AbigailRating, 5 stars1 month ago
Great place! Lots of activities at the house. Clean & Tyler was very communicative!
Top guest favorite
A cozy living area is highlighted by a fireplace and large windows allowing natural light. A round coffee table is positioned at the center of a comfortable seating arrangement that includes a sectional sofa and armchairs. Potted plants add a touch of greenery.
Home in Prospect
5 out of 5 average rating, 101 reviews

Stay at Peppermint Cottage in Norton Commons!

AunnaRating, 5 stars1 day ago
This was by far the best AirBnB my family has ever stayed in! From check-in to check-out Nicole was such a perfect host. The amenities at the peppermint cottage were absolutely perfect and all of the children’s items were SO helpful! We had the best week and will absolutely try to stay here again when in the area!
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, 27 reviews

Private Estate on Bourbon Trail w/ Beautiful Pool

SeanRating, 5 stars2 weeks ago
Spent the weekend for a bachelor party, this property was amazing!! Super private, plenty of space and great amenities. Our host had such great recommendations for distilleries, places to eat, and golf. Just an amazing stay and an amazing home. If you are looking for a place to stay along the bourbon trail, do yourself a favor and book this one!!
Superhost
A bright living area features a light gray sofa with two yellow accent pillows. A wooden coffee table sits in front, complemented by a small plant. The room flows into a dining space with dark chairs and a table, illuminated by natural light from large windows.
Home in Taylorsville
4.82 out of 5 average rating, 45 reviews

The Cozy Lake Place Cottage 75

CaraRating, 5 stars1 month ago
Great stay for a quick vacation.
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
4.82 out of 5 average rating, 162 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

RobertRating, 5 stars6 months ago
It was perfect for our needs. Very clean and close to 3 distilleries. The kitchen is well stocked with pots pans bakewear etc, and clean. bedrooms and baths are clean and comfortable. The hot tub and pool were clean and ready for us with plenty of space outside to sit and relax. over all it was a great location and very well taken care of.

Weekly house rentals

Top guest favorite
A cozy living area features a brown leather sofa positioned against a wall, complemented by a light rug and a coffee table. The open layout showcases a modern kitchen with cabinetry and an island, allowing natural light to fill the space through multiple windows.
Home in Shelbyville
5 out of 5 average rating, 9 reviews

The Country Pleasure Farm

CarolynRating, 5 stars3 weeks ago
This is a fabulous place. Gabriella has thought of everything! The home is newly remodeled and not only beautiful but so comfortable. She has thought of every amenity! This location is central to Louisville, Frankfort and Lexington making the Bourbon Trail Distilleries easy to visit! Many great restaurants in easy driving distance. I definitely would love to visit again!
Top guest favorite
The exterior of a spacious brick home is surrounded by well-maintained greenery and a manicured lawn. A welcoming front porch is adorned with a classic white door, framed by small shrubs and an American flag. The sky features a mix of clouds and blue tones.
Home in Shelbyville
5 out of 5 average rating, 6 reviews

The Knob in Shelbyville

ChrisRating, 5 stars7 months ago
This was a great place for five of us enjoying the bourbon trail. It is within 30 minutes of Buffalo Trace and Louisville, and an hour from Bardstown. Really enjoyed the back porch. Cooked dinner 3 nights and it felt at home. There is plenty of cooking pots/pans/utensils. Mark is a great host and was responsive.
A spacious house is set on a well-maintained grassy area, framed by trees in the background. A circular driveway leads to the entrance, where manicured shrubs and flower beds provide a natural touch. The home's neutral façade and stone accents blend harmoniously with the surroundings.
Home in Louisville
5 out of 5 average rating, 3 reviews

Southerland Vacation Home

MichaelRating, 5 stars2 months ago
This is a jaw dropping, breath taking, absolutely stunning property!!! Pristine clean, beautiful surroundings, incredibly spacious, lacking nothing! I was deeply moved by Madge’s kindness and generosity when she offered to give us a ride in her four wheel drive vehicle due to inclement weather. She was intentional in communicating with me and making sure everything went smoothly. I don’t have the words to express how comfortable, enjoyable, and pleasant our stay was! What a lovely experience!!! Thank you so much Madge!!!
Guest favorite
The exterior of a two-story brick house is shown, featuring a symmetrical design with a covered entryway and large windows. Lush green shrubs frame the front, and a welcoming porch is adorned with seating, providing a view of the manicured lawn.
Home in Simpsonville
5 out of 5 average rating, 16 reviews

Derby Getaway

TheresaRating, 5 stars11 months ago
Paula’s place was great! She left us bourbon chocolates, rain ponchos and an extra phone charger to borrow for the derby! Thankfully we didn’t need to use the ponchos!
Home in Shelbyville
4.67 out of 5 average rating, 36 reviews

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

CristiRating, 5 stars1 week ago
This place was a little bit of heaven and it was extremely clean and just as discribed in the listing. And the backyard was amazing. It is perfect for couples or families with plenty of room. My husband and I really had a peaceful stay and we really got to relax after having very busy lives. I highly recommend this rental. if I could have given this rental more than five stars I would have
Home in Shelbyville
5 out of 5 average rating, 3 reviews

Hillside view/ bourbon trail fun game room

StephanieRating, 5 stars5 months ago
Jamie was wonderful at answering questions quickly, helping with checkin promptly, and the home was exactly as described. Kitchen has all tools needed for cooking. Bedrooms and bathrooms all fully stocked with fresh linens, soaps, & Q-tips. Home is charming with plenty of room inside and out.
Guest favorite
The exterior of a red A-frame house features a sloped roof and large triangular windows, surrounded by well-maintained grass and shrubbery. A driveway leads to the entrance, while clusters of trees add to the natural setting in the background.
Home in Crestwood
4.94 out of 5 average rating, 18 reviews

Private 5 acre A frame

MarkRating, 5 stars9 months ago
Everything was clean and we had an amazing time in the pool. We loved this place so much we will be visiting again.

Private house rentals

Superhost
A charming two-story home features a welcoming front porch adorned with yellow accents and a seasonal wreath. Lush green trees provide shade, while a flag adds a festive touch. The well-maintained yard showcases a mixture of grass and fallen leaves, enhancing the home’s inviting exterior.
Home in Shelbyville
4.7 out of 5 average rating, 10 reviews

Charming Home in Historic Downtown Shelbyville

KellyRating, 5 stars1 month ago
Location was very convenient between Frankfort and Louisville. Easy to find the house. Street parking was not an issue. House was comfortable and exactly as described. We didn’t cook in the house so I can’t make any comments about the kitchen but it appeared to be well stocked. Coffee shops and Mexican restaurants very close to the house were amazing. Will stay here again for sure. Host could not of communicated faster. A+ rating!!
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 stars4 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!!
Superhost
A stylish living area features a black sofa and elegant wooden flooring. A circular wall decoration complements the wooden ceiling, while a fireplace provides warmth and ambiance. Natural light enhances the inviting atmosphere, with tasteful artwork adding character to the room.
Home in Shelbyville
4.77 out of 5 average rating, 52 reviews

Pool*HOT TUB*Bourbon Trail

GiovanniRating, 5 stars1 month ago
Amazing place, would stay here again, thank you Tony!
Guest favorite
A well-lit hallway is showcased, featuring light hardwood flooring and a wooden staircase with black iron railings. White walls create a clean look, while doors to rooms are seen on either side, enhancing the space's openness.
Home in Simpsonville
4.94 out of 5 average rating, 108 reviews

Comfortable sleek home bourbon trail

KayLeeRating, 5 stars2 weeks ago
Great place to stay. Very clean, 3 full bedrooms and 2 full baths. Book it!
Guest favorite
A welcoming entrance features a covered porch with two white columns and steps leading up to a black front door. A decorative lantern hangs beside the door, and a flower box adds a touch of greenery beneath the window, casting soft shadows on the facade.
Home in Simpsonville
4.9 out of 5 average rating, 31 reviews

Derby Bourbon Trail Classic

LeonardRating, 5 stars3 weeks ago
My family enjoyed the stay at this home very much. There was plenty of space and more than enough bedrooms. The home was well equipped with everything they needed to have away from home. My daughter said she would highly recommend this home to travelers visiting Shelbyville, Louisville and Lexington areas for the various activities and events in Kentucky.
Superhost
A single-story home is set on a spacious lawn, surrounded by neatly trimmed shrubs and colorful flower beds. Tall trees provide shade, while a satellite dish is positioned on the roof. The exterior features a combination of brick and siding with large windows that allow natural light.
Home in Simpsonville
4.71 out of 5 average rating, 21 reviews

Country Living

MaryBethRating, 5 stars4 months ago
What a fantastic week at EHfarms! It was perfectly set in the rolling hills of Kentucky. It was a beautiful farm that was great for the dogs! I needed a quiet country place and I would go back in a heartbeat.
Top guest favorite
A wooden dock extends over calm waters, framed by trees along the shoreline. Two sturdy metal ladders rise from the dock, providing access to the water below. The scene is illuminated by soft natural light, showcasing a peaceful lakeside environment.
Home in Shelbyville
4.96 out of 5 average rating, 72 reviews

Bass N Bourbon Retreat - Lakefront * Bourbon Trail

JulieRating, 5 stars6 months ago
The home was spacious, clean and well kept. We especially enjoyed the deck and picture window overlooking the lake. A great spot for 2 couples to relax and enjoy what Kentucky has to offer. Very close proximity to the Bulleit Distillery, which held its Autumn Fest during our stay. Highly recommend
The exterior of a restored farmhouse is presented with a welcoming porch featuring two rocking chairs. A large tree with autumn leaves stands in the foreground, surrounded by a grassy yard. Large windows allow for natural light, enhancing the serene countryside setting.
Home in Pleasureville
New place to stay

Bourbon Trail Country Getaway

JondaRating, 5 stars2 weeks ago
Just the kind of place you hate to leave! “The Old Farmhouse” has been meticulously restored, and beautifully furnished. It’s situated on a quiet road, surrounded by farmland. We so enjoyed watching the cows graze from the front porch swing. The kitchen is spacious and had everything we needed for cooking, and then some! Beds were very comfortable, with quality linens and the entire home was squeaky clean. What a delightful stay!

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