House vacation rentals in Shelby County

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Popular amenities for Shelby County house rentals

House rentals with a pool

Guest favorite
An aerial view captures the community resort pool surrounded by a spacious deck with lounge chairs. The pool is enclosed by a white fence, while lush greenery and trees offer a backdrop. A small shed is visible in the distance amid the open grassy area.
Home in Taylorsville
4.91 out of 5 average rating, 23 reviews

Bourbon Trail Lake Home w/ Hot tub & King Bed

SteveRating, 5 starstoday
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!
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, 45 reviews

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

HeatherRating, 5 stars1 week ago
This house was beautiful! Kaeley had everything you could think of (and everything you may have forgotten like coffee or coffee creamer!) the entire premises is an absolute dream, you almost don’t even need to go do anything else because there’s so much to do on property! It was the perfect central spot for some of the farther away things as well like mammoth cave and/or the further away distillery’s! And only 30 mins from Louisville! It was the perfect trip, and the perfect spot and I have no complaints or nothing negative to say about the property!! It was perfect!!
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
4.96 out of 5 average rating, 28 reviews

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

JenniferRating, 5 stars2 days ago
Loved Jill’s place!! It was so beautiful and thoughtfully decorated. Enjoyed our stay there so much!
Guest favorite
A large outdoor pool is surrounded by a concrete patio, featuring several loungers positioned for relaxation. In the background, a well-maintained landscape includes a wooden fence and various buildings nestled among trees, indicating a serene rural setting.
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!!
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 stars5 days 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
Home in Prospect
5 out of 5 average rating, 107 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

BetsieRating, 5 stars1 week 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, 29 reviews

Private Estate on Bourbon Trail w/ Beautiful Pool

KaceyRating, 5 stars2 weeks ago
This property is so beautiful and peaceful! We went with our family of four and my parents. My dad is struggling with mobility so David allowed us to drive him to the pond to fish. My family really enjoyed the scenery, farm sounds & beautiful home!
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 stars2 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!!

Weekly house rentals

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, 7 reviews

The Knob in Shelbyville

KarenRating, 5 stars1 month ago
This place was very nice! It met all my expectations and then some. It had everything you needed from puzzles to cookbooks. The decor was very nice it was clean and smelled good. Shopping was conveniently located from Walmart to the Outlet. The spacing was great for all the guest from the very comfortable patio with a firepit to the Livingroom with a very comfortable sofa to the dining area with plenty of seating. If you were cooking, the kitchen was equipped with everything needed and enough space for conversations while cooking. Overall it was a great House :-)
Top guest favorite
A spacious outdoor patio features a round table surrounded by two sturdy, high-backed chairs. The setting is complemented by a vibrant green tree and expansive views of the surrounding countryside, providing a serene space for relaxation.
Home in Shelbyville
5 out of 5 average rating, 13 reviews

The Country Pleasure Farm

AndrewRating, 5 stars1 week ago
We had a wonderful stay—thank you, Gabriella, for creating such a great place to visit. The house sits on a beautiful farm property, which added a peaceful, private feel to the whole trip. What really stood out was the attention to detail inside the home. While it’s clearly set up as a rental, nothing about it felt generic or thrown together. The furniture and decor were high quality, thoughtfully chosen, and made it feel like we were staying at a friend’s home rather than just another Airbnb. Gabriella, you’ve done a fantastic job creating a warm, inviting space. We’d absolutely come back.
A charming 1920s stucco home is displayed against a clear blue sky. The exterior features a dark metal roof and large windows, surrounded by a well-maintained lawn and landscaping. Trees in the background indicate the rural setting of the property.
Home in Shelbyville
5 out of 5 average rating, 4 reviews

Hillside view/ bourbon trail fun game room

WillRating, 5 stars2 weeks ago
Our family of four had a wonderful Memorial Day weekend here and would definitely stay here again and recommend to anyone. Very beautiful and peaceful property. Great views, sunrise, sunset. Great lawn for yard games. Fully stocked with plenty of supplies. Kids loved the upstairs bunk room. Everyone loved the game room. We had to contact the host during our stay and she was very quick to respond and take care of our need.
A spacious living area is highlighted by a sectional sofa with decorative pillows. A modern ceiling fan is mounted above, and natural light enters through the nearby door. A small table with a lamp sits next to the sofa, adding functionality to the layout.
Home in Taylorsville
5 out of 5 average rating, 3 reviews

NEW ON SITE! Renovated 3bedrm home - 2King/1Queen

NicoleRating, 5 stars2 weeks ago
This was a great AirB&B! EXTREMELY clean and comfortable! High end towels, linens and bathroom rugs. The covered back deck was peaceful and comfortable. Very comfortable and peaceful for a weekend away! Will definitely visit again!
A living area featuring two brown leather sofas and a matching armchair, arranged around a round coffee table. Natural light enters through large windows, framed by light curtains. A decorative area rug adds texture to the wooden floor, while a wall-mounted TV completes the space.
Home in Shelbyville
4.73 out of 5 average rating, 64 reviews

NEAR Bourbon Trail! Quiet Neighborhood!

JoshRating, 5 stars2 weeks ago
Good place as described. Nice central location. Host was responsive and house was clean and exactly what we needed.
Guest favorite
A charming outdoor area features a multi-level deck with a bright umbrella over a seating area. Red Adirondack chairs are surrounded by lush greenery and flowering plants. A gazebo with string lights offers a cozy space for relaxation, while a pathway connects various sections of the garden.
Home in Louisville
5 out of 5 average rating, 8 reviews

Red Bridge Retreat

YuriamnaRating, 5 stars2 weeks ago
We had a fantastic stay! The house was absolutely perfect, clean, comfortable, spacious, and beautifully maintained. The kitchen was incredibly well equipped with everything you could possibly need, which made cooking and mealtime so easy and enjoyable. The hot tub was a huge bonus, perfect for unwinding at the end of the day. And the house was great for kids too, with plenty of space and activities to keep them entertained both indoors and outdoors, which made the whole experience relaxing and fun for the whole family. We truly felt at home and would absolutely love to stay here again. Highly recommended!
Top guest favorite
A single-story home with a welcoming front porch is surrounded by well-maintained lawns and shrubs. The structure features multiple windows and a gabled roof, with warm evening light illuminating the exterior. A paved path leads to the entrance, enhancing accessibility.
Home in Simpsonville
5 out of 5 average rating, 10 reviews

The Haven Simpsonville* Bourbon Trail* 3 bed/3bath

BridgetRating, 5 stars2 weeks ago
Could not ask for a better place to stay for a weekend! Loved the personal touch of fresh peonies around the house, beds were comfortable and each room had a sound machine for a more restful sleep as the place is off the road. Location made it walkable to a coffee shop we enjoyed. We also loved coming back to the place after a busy day out and using the beautiful outdoor space to unwind. Would recommend!
Top guest favorite
A cozy living room features a light-colored sofa set with stylish details, positioned around a central wooden coffee table. Large windows allow natural light to fill the space, while decorative mirrors and plants add visual interest to the warm, inviting atmosphere.
Home in Shelbyville
5 out of 5 average rating, 24 reviews

Last Minute Discount/Hot Tub/Fire Pit/Game Room

McCallRating, 5 stars6 days ago
We had a great stay! Centrally located for the bourbon trail! Judy was very helpful with recommendations and quick to respond! If you are ever in Shelbyville I’d highly recommend The Bell House and McKinley’s!

Private house rentals

The exterior of the home is showcased with a well-maintained brick facade and a pitched roof. A spacious driveway leads to the entrance, framed by manicured landscaping and shrubs. A decorative mailbox stands in front, completing the welcoming appearance.
Home in Louisville

Premier home in Louisville near Valhalla Golf Club

TerriRating, 5 stars13 months ago
Ken and Brenda’s home is absolutely immaculate. Exceeded expectations, I met their grandson as I checked in, incredibly accommodating, could not ask for a better place for our guests to stay. I would definitely stay at their home again. Wonderful experience.
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, 17 reviews

Derby Getaway

MarianRating, 5 stars8 months ago
Spacious, beautiful home! Lots of room to relax and spend time with friends while visiting the area.
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 stars3 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 features a two-story white house with a red front door, surrounded by greenery. A concrete pathway leads to the entrance, and a spacious driveway complements the landscape. Soft outdoor lighting highlights the home's contemporary design during dusk.
Home in Simpsonville
4.95 out of 5 average rating, 113 reviews

Comfortable sleek home bourbon trail

PatrickRating, 5 stars2 weeks ago
Very comfortable beds and room to spread out for 6 guests and two pups. Great value for such a nice space.
Guest favorite
A large luxury home is showcased with a stone and brick facade. Lush green grass surrounds the property, complemented by well-maintained shrubbery and trees. A slight incline leads to the entryway, which features steps flanked by flowerbeds, all against a clear blue sky.
Home in Louisville
5 out of 5 average rating, 7 reviews

Bourbon trail luxury 4 bdrm getaway!

KarenRating, 5 stars5 days ago
We had a wonderful stay and felt more than at home. No detail was left out. I felt like I was staying at a five star resort. There was plenty of room for everyone to have their own space but still have wonderful spots to gather and enjoy each other's company. The home was exceptional in all areas. We would love to stay again and I highly recommend the home to anyone visiting the Louisville area.
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
4.95 out of 5 average rating, 19 reviews

Private 5 acre A frame

KevinRating, 5 stars9 months ago
Great outdoor space and great entertainment in the basement!
The charming exterior of the home features a covered porch with two rocking chairs. White trim and decorative touches adorn the front, while a well-maintained lawn and trees provide a peaceful setting. A stone pathway leads to the front door.
Home in Bagdad
4.86 out of 5 average rating, 7 reviews

Convenient to Bourbon Trail, Keeneland and C Downs

LashbrookeRating, 5 stars1 month ago
This is one of our favorite spots, will definitely be rebooking!!!! The home is so relaxing and a nice place to hang out with friends.
Guest favorite
A hot tub filled with water sits invitingly, surrounded by greenery and a clear sky. A glass of whiskey rests on the edge, complementing the tranquil setting. The bubbles within the hot tub suggest relaxation awaits in this outdoor space.
Home in Simpsonville
4.96 out of 5 average rating, 23 reviews

*Distilleries close by* Hot tub*Firepit

ChristianRating, 5 stars3 weeks ago
Toni's place was the perfect house for our group outing on the Bourbon Trail. The house is surrounded by miles of beautiful Kentucky countryside and estates, and it has easy access to the cities and all the stops on the Bourbon Trail. The house is new and clean and has all the amenities you need to enjoy your time relaxing and planning your next adventure. I would highly recommend this house for anyone who's looking for a central location to enjoy all that Bourbon Country has to offer.

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