Family-friendly holiday rentals in Frankfort

The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.

4.99 out of 5 average rating, 126 reviews

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

Indoor spacesFamilyWi-Fi

5.0 out of 5 average rating, 122 reviews

Bourbon Central Waterfront Luxe near Buffalo Trace

This Ultra Luxe River Flat located in the heart of the Capital City of Frankfort, Ky offers 1600 square feet of step free luxurious, modern living within walking distance to everything downtown has to offer- 15+restaurants/pubs. 1.8 miles to Buffalo Trace, less than 10 miles to Woodford Reserve, Castle & Key and Whiskey Thief. -King Size Bed Suite -Heated floors in main bath -1 Gig Wifi -75" /55" Smart TVs/Direct TV/Apps - Coffee Station w/Decaf and tea - Piano, Guitar - Golden Tee Ms. Pac-Man

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 163 reviews

A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.

Farm stay in Frankfort

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

FamilyIndoor spacesView

5.0 out of 5 average rating, 240 reviews

A well-equipped kitchen features dark wooden cabinetry and granite countertops. Four barstools with cushioned seats are arranged around a large island. Stainless steel appliances, including a refrigerator and oven, are visible alongside natural light streaming through a window.

Cabin in Frankfort

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

Indoor spacesFamilyAccess

4.99 out of 5 average rating, 573 reviews

A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.

Train in Lawrenceburg

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Indoor spacesKitchenGetting around

A charming bungalow exterior is highlighted by vibrant green siding and white accents. A covered porch with intricate railing invites guests, while a pathway leads through well-maintained landscaping adorned with flowers and fresh grass. The setting sun casts a warm glow over the home.

4.97 out of 5 average rating, 127 reviews

River Row Bungalow

Come visit the River Row District. Located in the heart of Downtown Frankfort. Within walking distance to shops, dining, bourbon, live music and the Capitol Building! Discover what Frankfort has to offer during the day. Come home to relax in the hot tub and enjoy a fire in the yard. Have your morning coffee and relax in the swing under the covered porch, while listening to the church bells. Sleeps 8 with two king beds, 1 queen bed and two twin beds in a loft space within the queen bedroom.

Indoor spacesKitchenAmenities

The exterior of the home features a welcoming porch with rocking chairs framed by neatly trimmed hedges. A manicured lawn with shrubs enhances the inviting approach to the entrance. Surrounding trees provide a natural backdrop, contributing to the overall charm of the property.

4.93 out of 5 average rating, 256 reviews

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

Wake up & smell the mash! Located just steps away from Buffalo Trace Distillery. Enriched with history & tradition is where you will find Wilkinson. This historic home has recently undergone renovations & no expense was spared. Guests will enjoy the walkability to Downtown Frankfort & many of the local attractions. Featuring 2 bedrooms & 2 baths, guests are able to experience life like a local with all the modern-day amenities. We are also only a 7.2-mile drive to Castle & Key Distillery.

FamilyIndoor spacesNearby

4.96 out of 5 average rating, 111 reviews

A charming two-story building features a white exterior with blue accents and a sloped roof. A large wooden ramp leads to the entrance, surrounded by lush green trees and landscaped areas, creating a welcoming environment for guests.

Guest suite in Frankfort

Studio 1101

Second story one bedroom studio above small hair salon. Unique building conveniently located near historic downtown, major highways, restaurants and distilleries. Wi-Fi and on-site illuminated parking available as well. A window A/C unit (added 8/25) helps keep the 2nd story space cool during summer months. W/D svc available on stays over 5 days. The salon generally closes at 6 p.m. T-Th so there will be no traffic or noise after that time. The salon is also closed Sunday and Monday.

KitchenIndoor spacesAccuracy

4.97 out of 5 average rating, 246 reviews

A large window allows natural light to brighten the entrance area, showcasing a view of the street and nearby shops. A modern light fixture hangs from the ceiling, complementing the open and airy feel of the space.

Apartment in Frankfort

Bing’s Downtown Guest Suite on Main

Make your home away from home at this centrally-located guest suite encompassing the entire second floor of the historic Bing’s Building in the center of downtown Frankfort, Kentucky! Historic downtown guest suite with modern amenities located in the heart of the capital city. Within blocks of great dining, shopping, entertainment, and historic sites. A short distance to Buffalo Trace and other popular distilleries, Keeneland racetrack, bluegrass horse country and much more!

KitchenIndoor spacesCondition

A charming exterior view of a two-story bungalow features blue-green siding and a welcoming front porch. American flags are displayed, while flower beds with various plants enhance the landscaped front yard. The stone walkway leads to the entrance, inviting visitors to approach the home.

4.98 out of 5 average rating, 103 reviews

The Crafty Bourbon Bungalow Apartment

The Crafty Bourbon Bungalow Apartment is located in the historic district of Frankfort just three blocks from the Capitol and within walking distance of downtown shops and restaurants. We are in the heart of horse and bourbon country with easy access to local distilleries and racetracks. The apartment has a private entrance, one parking space, two bedrooms with queen beds, one bath with claw tub/shower combo, kitchenette and an eating and sitting area.

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 189 reviews

The living area features exposed brick walls and hardwood flooring. A flat-screen TV is mounted above a decorative fireplace, providing entertainment options. Natural light fills the space through large windows with white trim, complemented by a dark wooden coffee table and modern seating.

Apartment in Frankfort

Historic Loft in Frankfort Entertainment District

Experience the charm of a newly renovated 2-story loft in the Historic St. Claire Entertainment District of Frankfort, KY. Immerse yourself in the best of Kentucky, with convenient access to world renowned distilleries like Buffalo Trace and Woodford Reserve or catch the excitement of live thoroughbred racing at Keeneland Racetrack, just a short drive away in Lexington, KY. This special place is close to everything, making it easy to plan your visit.

Indoor spacesKitchenParks

4.98 out of 5 average rating, 452 reviews

A charming tiny house is nestled in a natural setting, featuring a metal roof and wooden exterior. A small porch with seating is visible, surrounded by greenery. The yard is complemented by a grassy area and a wooden fence, enhancing the serene environment.

Tiny home in Frankfort

Tiny Home with Huge Charm near the Elkhorn Creek

Just minutes from downtown Frankfort, this place is a little peaceful country getaway with a lot to offer! It’s nestled on a quiet street with great access to the beautiful Elkhorn Creek! If you’re into Bourbon tours, Horses, canoeing/kayaking/fishing, or Natural and Historical sites, this place is a great location in the middle of a lot to see and do! The tiny house has a small kitchen and bath as well as a yard and private patio and grill to enjoy!

KitchenIndoor spacesHiking

Popular amenities for Frankfort family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 102 reviews

Hot Tub > 3 King Beds > 7 mins to Buffalo Trace

FamilyIndoor spacesCheckout

4.99 out of 5 average rating, 293 reviews

Cabin in Lawrenceburg

Relax in the hot tub with a view of the River!

Indoor spacesFamilySleep quality

4.98 out of 5 average rating, 254 reviews

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

KitchenIndoor spacesNearby

A bright living area features a comfortable gray sofa adorned with colorful throw pillows. A round coffee table sits atop a soft area rug, complemented by wooden chairs nearby. Natural light streams through multiple windows, creating a welcoming atmosphere in this open space.

4.99 out of 5 average rating, 194 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Indoor spacesFamilyDecor

4.97 out of 5 average rating, 159 reviews

Two wooden Adirondack chairs are positioned around a stoned fire pit, overlooking a tranquil lake. The scene features lush greenery and a group of ducks gently swimming in the water, complemented by a boathouse and kayaks in the background.

Cabin in Lawrenceburg

Bourbon Trail Bliss by the Lake, HotTub, Kayaks

Indoor spacesKitchenComfort

4.98 out of 5 average rating, 159 reviews

Home in Bagdad

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

KitchenFamilyCheck-in

4.98 out of 5 average rating, 256 reviews

Dome in Mount Washington

My Old Kentucky Dome

Indoor spacesKitchenCheck-in

4.83 out of 5 average rating, 178 reviews

A hot tub is illuminated with blue LED lights, creating a serene atmosphere in a cozy corner. The tub features multiple seating positions and control buttons for easy adjustments. A wooden bench is placed nearby, offering a place to relax before or after use.

Home in Lawrenceburg

Restful Bourbon Trail Lodge with Pool and Hot Tub

KitchenIndoor spacesDecor

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 152 reviews

An exterior view of the charming upstairs unit is presented, showcasing a wooden staircase leading to a covered porch. The building features a brick facade, with greenery surrounding the entrance. A cloudy sky is viewed above, giving a subdued ambiance.

Barn in Midway

Modern horse barn

FamilyIndoor spacesBarbecue

A charming gray house is situated on a gently sloping lot, framed by a clear blue sky. The entryway features a small porch with two chairs and potted yellow flowers. An American flag is displayed on the front, enhancing the home's welcoming exterior.

4.9 out of 5 average rating, 106 reviews

The Bourbon Sanctuary

FamilyKitchenBathroom

4.97 out of 5 average rating, 143 reviews

A spacious studio features an industrial design with exposed brick and weathered walls. A cozy Queen Murphy Bed is dressed in neutral linens and accented with decorative pillows. A stylish plant adds a touch of greenery, while well-placed lighting creates a warm ambiance.

Apartment in Shelbyville

Unique Downtown Studio with an Industrial Vibe

KitchenIndoor spacesAmenities

A charming two-story house features a blue exterior with stone accents and a welcoming front porch. Green grass and well-maintained landscaping frame the walkway, while blooming flowers add a touch of color. The home is situated in a peaceful neighborhood.

4.98 out of 5 average rating, 287 reviews

Blue's Bourbon Bungalow

KitchenIndoor spacesPets

4.98 out of 5 average rating, 450 reviews

A two-story brick house is set among green grass and trees, with a gravel driveway leading to it. A black wooden fence borders the property, and vibrant yellow flowers are visible in the foreground. The outdoor space exudes a sense of openness and tranquility.

Farm stay in Georgetown

Great Crossings Goat Farm & Apiary

KitchenFamilyHospitality

4.96 out of 5 average rating, 401 reviews

A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.

Home in Lexington

Horse Farm Creekside Cabin- 6 min to KY Horse Park

FamilyKitchenLayout

4.98 out of 5 average rating, 275 reviews

An outdoor space features a fire pit surrounded by four adirondack chairs and two wooden benches. The gravel area is set against a backdrop of lush greenery, with the cabin visible in the distance. Bright red umbrellas provide shade over the seating area.

Cabin in Sadieville

*Unique Wooded Cabin*4 beds 20 min from The Ark

KitchenIndoor spacesCheckout

4.96 out of 5 average rating, 243 reviews

A restored farmhouse is shown with a charming white exterior and a black roof. The front porch features white railings, while the surrounding lawn is well-maintained with a grassy area and some trees in the background.

Chalet in Lawrenceburg

Countryside On the Bourbon Trail, 22 Quiet Acres

FamilyIndoor spacesHeating

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 155 reviews

A cozy living area is presented with a television mounted on the wall. A black leather sofa faces a small wooden coffee table and two armchairs. Natural light filters through the windows, complemented by patterned curtains, creating a warm atmosphere.

Cottage in Salvisa

Cottage on the Bourbon Trail

KitchenFamilyNearby

4.97 out of 5 average rating, 188 reviews

A spacious living and dining area features a full-sized, counter-height dining table with six chairs. A cozy seating area includes a sofa and a secondary sleeping area with a twin bed and trundle. Decorative shelving displays various kitchenware and the room is softly illuminated by natural light.

Farm stay in Georgetown

Beautiful farm stay apartment, rural Georgetown KY

Indoor spacesFamilyValue

4.99 out of 5 average rating, 152 reviews

A living area features comfortable seating arranged around a wooden coffee table. A stone fireplace with an electric insert is positioned beneath a flat-screen television mounted on the wall. The warm red walls create a cozy backdrop, and kitchen facilities are visible in the background.

Cottage in Taylorsville

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

FamilyKitchenWi-Fi

4.96 out of 5 average rating, 162 reviews

Two horses are depicted, one dark brown and the other light chestnut, standing side by side. They are adorned with riding gear, their eyes focused on the landscape ahead, which features rolling hills blanketed in greenery and autumn foliage.

Farm stay in Harrodsburg

The Bunkhouse at Big Red Stables

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 126 reviews

An open-concept living area features high ceilings supported by dark beams. A comfortable sofa and a rug are positioned on the wood floor, while a kitchen with colorful bar stools is visible in the background. Large windows allow natural light to fill the space.

Home in Georgetown

Modern Farmhouse/20 acres/9 miles from Horse Park

Indoor spacesFamilyLocation

4.91 out of 5 average rating, 148 reviews

Cottage in Taylorsville

Lakeside Haven Cottage 4, Lake View, Hot Tub, Pool

Indoor spacesFamilySleep quality