Family-friendly vacation 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, 135 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.

KitchenIndoor spacesBathroom

5.0 out of 5 average rating, 252 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!)

KitchenFamilyGetting around

4.99 out of 5 average rating, 169 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.

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 593 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.

4.96 out of 5 average rating, 135 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.

KitchenIndoor spacesLocation

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, 267 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.

Indoor spacesFamilyTV

5.0 out of 5 average rating, 120 reviews

Home in Lawrenceburg

Bourbon Speakeasy 6BR Estate · Hot Tub · Sleeps 14

Bourbon Trail Hideaway – Where Luxury Meets Fun Gather your favorite people and settle into this stunning 6-bedroom, 4.5-bath modern farmhouse, built for connection, comfort, and fun. With room for up to 14 guests, enjoy spacious living areas, relaxing spa amenities, and entertainment everyone will love. Whether you’re here for the Bourbon Trail or simply to unwind together, this home delivers an unforgettable stay. 🥃 Reserve your dates today and make it a trip to remember.

FamilyKitchenSleep quality

Superhost

A bright bedroom showcases a spacious bed with a light-colored quilt, complemented by a decorative patterned area rug. Two windows provide natural light. A chair and desk are present, along with a small striped couch and a bedside lamp, creating a functional and inviting space.

4.84 out of 5 average rating, 139 reviews

Capitol Walk/7min to Buffalo Trace

Walking distance to the State Capitol, this historic home has recently undergone renovations & no expense was spared. Featuring 3 bedrooms & 2.5 bathrooms, guests are able to experience life like a local with all the modern-day amenities. Walking distance to Downtown Frankfort & only a 7-mile drive to Buffalo Trace and 15 minutes to Castle & Key Distillery. Guests can even walk to Rebecca Ruth Candy or Andy's Bakery! Property features on-street parking.

KitchenIndoor spacesHospitality

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, 109 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.

FamilyIndoor spacesDecor

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, 197 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, peaceful home, thoughtfully designed with comfort and style in mind. This cozy haven offers a relaxing place to unwind after a day of exploring bourbon country. Just minutes from Castle and Key and Woodford Reserve and only ½ mile from the highly rated restaurant and bourbon bar, The Stave. Whether you’re here for tastings, scenic drives, or quiet evenings in, Limestone Landing puts you right where you want to be!

FamilyKitchenOutdoor spaces

4.99 out of 5 average rating, 224 reviews

A well-equipped kitchen features a spacious wood island with two upholstered stools. Modern appliances, including a gas range and sleek cabinetry, complement the space. Natural light streams through the windows, enhancing the inviting atmosphere, while tasteful decor adds a touch of character.

Loft in Frankfort

The Loft - Cozy Retreat in Historic Downtown

The Loft isn't just a place to stay; it's the feeling of finally slowing down. This cozy, light-filled retreat invites you to wake up easy, explore bourbon country, wander historic Frankfort, and return to a space that feels instantly like home. Thoughtfully designed with warm textures, modern comforts, and a peaceful atmosphere, it's the perfect escape for couples, solo travelers, and weekend adventurers seeking a memorable Kentucky getaway.

KitchenIndoor spacesBreakfast

4.99 out of 5 average rating, 106 reviews

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

Welcome to BOURBON HOLLOW! 🦬 Buffalo Trace - 3.5 miles/7 minutes 🔑 Castle & Key - 8 miles/15 minutes Whiskey Thief - 9 miles/15 minutes 🥃 Woodford Reserve - 14.2 miles/21 minutes 🦃 Wild Turkey - 15.2 miles/23 minutes 🌹 Four Roses - 18 miles/23 minutes 🥃 Bulleit - 15.4 miles/24 minutes 🎩 Jeptha Creed - 25.6 miles/28 minutes Lexington Area Distilleries - 31 miles/35 minutes Louisville Area Distilleries - 52 miles/52 minutes

FamilyKitchenCondition

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, 115 reviews

Home in Midway

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

FamilyIndoor spacesParking

5.0 out of 5 average rating, 162 reviews

A log cabin is set against a vibrant sunset, highlighting its wooden exterior and spacious porch. Lush green grass surrounds the cabin, complemented by flower beds and gravel pathways. The rear showcases windows and entrance doors that invite natural light into the home.

Cabin in Frankfort

Sip on bourbon in the hot tub! +hiking & game shed

FamilyKitchenTV

4.99 out of 5 average rating, 301 reviews

Cabin in Lawrenceburg

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

Indoor spacesFamilyRiver

An aerial view of a red-brick house surrounded by lush greenery and open fields. The property features a gravel driveway, outdoor seating areas, and a covered patio. Scenic hills can be seen in the background, creating a peaceful country atmosphere.

4.93 out of 5 average rating, 107 reviews

Hillside Hideout With Hot Tub - Scenic Bluegrass

Indoor spacesFamilyPets

4.99 out of 5 average rating, 267 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 spacesCleanliness

4.98 out of 5 average rating, 162 reviews

Home in Bagdad

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

FamilyKitchenBathroom

4.98 out of 5 average rating, 263 reviews

Dome in Mount Washington

My Old Kentucky Dome

KitchenFamilyAccess

4.97 out of 5 average rating, 153 reviews

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

Home in Lexington

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

Indoor spacesKitchenComfort

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 115 reviews

The bedroom features a spacious bed adorned with various pillows and a textured throw. A cozy seating area is included, complemented by a stylish rug. Natural light enters through two large windows, and a desk and decorative art piece enhance the modern decor.

Apartment in Frankfort

The "Main Stave" - Luxury Downtown Apartment

FamilyKitchenValue

4.98 out of 5 average rating, 161 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

FamilyKitchenLaundry

4.98 out of 5 average rating, 457 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

Indoor spacesKitchenTV

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, 108 reviews

The Bourbon Sanctuary

FamilyIndoor spacesCheckout

A two-story brick home is set among lush green landscaping, featuring a welcoming front porch. Large windows allow for ample natural light, while a manicured lawn and mature trees frame the property, creating a serene outdoor setting.

4.95 out of 5 average rating, 137 reviews

Large Family Gatherings and Bourbon Tours

FamilyIndoor spacesSleep quality

4.96 out of 5 average rating, 406 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

FamilyIndoor spacesLayout

4.95 out of 5 average rating, 287 reviews

The exterior showcases a rustic cabin with wooden siding, complemented by neatly trimmed bushes. A screened porch is visible, providing a welcome entrance with wooden flooring and a partial view of the outdoor area beyond.

Farm stay in Georgetown

Horse Country Heaven

KitchenFamilyOutdoor spaces

4.95 out of 5 average rating, 111 reviews

A seating area is furnished with two brown recliners and a matching couch, arranged around a light area rug. A television is placed on a wooden stand against the wall. Framed artwork decorates the neutral-colored walls, contributing to a cozy atmosphere.

Apartment in Georgetown

Private Farm Basement Apartment!

KitchenIndoor spacesLocation

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 108 reviews

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

The Bees Wing

KitchenIndoor spacesAccuracy

4.97 out of 5 average rating, 190 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

KitchenIndoor spacesCondition

4.82 out of 5 average rating, 180 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

Indoor spacesFamilySleep quality

4.95 out of 5 average rating, 131 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 spacesKitchenPool

4.96 out of 5 average rating, 164 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 spacesKitchenComfort

4.85 out of 5 average rating, 104 reviews

The exterior of the cottage features a charming façade with a covered porch framed by light-colored wood columns. A vibrant red door serves as a focal point, complemented by neatly trimmed shrubs and a landscaped area. Soft, natural lighting enhances the welcoming atmosphere.

Home in Taylorsville

Little Slice of Heaven-27

FamilyIndoor spacesWalkability

4.94 out of 5 average rating, 190 reviews

A two-story cottage is situated against a lush green backdrop. The exterior features light-colored siding, a covered porch, and multiple windows that allow natural light. A well-maintained lawn surrounds the home, enhancing the inviting appearance of the property.

Cottage in Taylorsville

The Gathering Place

FamilyKitchenWalkability