Family-friendly holiday rentals in Frankfort

5 out of 5 average rating, 112 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

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, 121 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.

4.99 out of 5 average rating, 158 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.

5 out of 5 average rating, 227 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!)

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, 119 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.

4.99 out of 5 average rating, 547 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!

4.95 out of 5 average rating, 258 reviews

A cozy sleeping area features a spacious bed with crisp white linens. An inviting sitting area with a white couch rests next to a wooden wardrobe. Natural light filters through nearby windows, highlighting the room's soothing decor and warm atmosphere.

Guest house in Frankfort

The Carriage - Quaint Haven steps to the Capitol

Your perfect Kentucky getaway starts here. Tucked in Historic Frankfort, this charming Parisian-inspired retreat is minutes from 13 renowned bourbon distilleries, the Kentucky Capitol, and downtown favorites. Spend your days tasting, exploring, and discovering local history, then unwind with a glass of your perfect drink on your private bistro deck. Thoughtfully designed for comfort and relaxation, this cozy hideaway is the ideal home base for an unforgettable Bourbon Country escape.

4.93 out of 5 average rating, 313 reviews

Two outdoor bathtubs are positioned on a wooden deck, surrounded by trees and views of the creek. An Adirondack chair sits nearby, providing a space for relaxation while enjoying the natural surroundings.

Treehouse in Georgetown

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

4.97 out of 5 average rating, 140 reviews

A well-maintained backyard area is highlighted by a green hammock suspended between trees. The brick apartment is elevated with a wooden deck and stairs leading to the entrance. Surrounding the space, manicured shrubs and grass create a peaceful outdoor environment.

Guest house in Frankfort

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

4.98 out of 5 average rating, 443 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!

4.99 out of 5 average rating, 116 reviews

A gravel path leads up to the cabin, surrounded by lush greenery and tall trees. The cabin's exterior features a mix of wood and metal siding, with a deck extending from the entrance, providing a connection to the natural surroundings.

Cabin in Lawrenceburg

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

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, 276 reviews

Blue's Bourbon Bungalow

A bourbon lover’s paradise. Located minutes from the worlds best Bourbon distilleries and within walking distance of several dining establishments. Enjoy walking the grounds of the state capital and touring several of Kentucky’s historical museums. Centrally located between the thriving cities Lexington and Louisville, Frankfort is the perfect home base to explore everything Kentucky has to offer.

Popular amenities for Frankfort family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 192 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

4.98 out of 5 average rating, 240 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

4.94 out of 5 average rating, 583 reviews

A polished copper bar counter reflects a variety of bourbon bottles and mixers. A cocktail shaker and glass sit ready for use, accompanied by a stylish ice bucket. The arrangement provides a glimpse into a well-equipped space for cocktail preparation.

Guest house in Lexington

The Bourbon House- Downtown Lex’s Premier Air B&B

4.82 out of 5 average rating, 123 reviews

A spacious cabin is set on a green lawn, featuring a wraparound porch supported by sturdy posts. The metal roof and wooden exterior harmonize with the surrounding trees. Rolling hills are visible in the distance under a cloudy sky.

Cabin in Harrodsburg

Governor's Private Cabin on Bourbon Trail w HotTub

4.97 out of 5 average rating, 151 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

4.96 out of 5 average rating, 193 reviews

The charming bungalow features a cozy front porch with wooden accents and an inviting entrance. The exterior combines green siding and natural wood shingles, surrounded by well-maintained landscaping. A pathway leads to the door, framed by neatly trimmed bushes, offering a welcoming sight.

Bungalow in Danville

WildernessTrace BarrelProof *Hottub/firepit*

4.89 out of 5 average rating, 189 reviews

The entrance features a solid door with a black finish, framed by blooming hydrangeas in a stone planter. Light glistens on the smooth gravel pathway leading up to the door, complemented by a modern wall-mounted light fixture.

Farm stay in Georgetown

The Stripping Room @ The Ranch

The cottage features a two-story structure with a light gray exterior and a welcoming entrance. A front staircase leads to a covered porch area, framed by well-maintained shrubs and greenery. Large windows provide natural light to the inviting living spaces within.

4.89 out of 5 average rating, 149 reviews

Lake Refuge near Louisville & Bourbon Trail #52

Family- and pet-friendly home rentals

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, 241 reviews

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

4.98 out of 5 average rating, 268 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

5 out of 5 average rating, 6 reviews

Flat in Frankfort

Downtown Frankfort*Location*House of Commons

Superhost

A charming, dark-colored cottage is set amidst lush greenery. A covered porch is visible at the front, featuring comfortable seating. Flower beds and manicured landscaping enhance the natural surroundings, while tall trees provide shade and tranquility.

Cabin in Versailles

4.87 out of 5 average rating, 101 reviews

Creekside- Bourbon Trail Oasis

4.95 out of 5 average rating, 169 reviews

An outdoor area is visible, featuring a fire pit surrounded by several chairs and a picnic table. Lush green grass is present, complemented by trees in the background. An active railroad bridge looms above, with soft, diffuse light filtering through the clouds.

Cabin in Wilmore

Highbridge River Cabin, Private Dock, EV Charger

4.96 out of 5 average rating, 239 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

4.94 out of 5 average rating, 175 reviews

The cottage exterior is framed by lush greenery and a neatly maintained lawn, featuring a charming porch with rocking chairs. A stone pathway leads up to the entrance, surrounded by trees and open space, providing a serene rural setting.

Home in Lexington

Charming Cottage Home on a Horse Farm in the City!

4.87 out of 5 average rating, 190 reviews

A comfortable living area features a brown leather sofa adorned with decorative cushions and a dark accent wall. A wooden coffee table sits in front, accompanied by a blue armchair. A lamp stands beside the sofa, illuminating the space, while natural light enters through the nearby door.

Townhouse in Frankfort

Bourbon Trail Lakehouse - Pet Friendly!

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 103 reviews

A rustic log cabin is partially visible through surrounding greenery. The cabin's wooden exterior is complemented by two windows and a centrally located door, which features a simple design. The natural landscape evokes a serene rural setting.

Cabin in Paris

1791 Cabin on Historic Horse Farm

4.96 out of 5 average rating, 158 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

4.91 out of 5 average rating, 144 reviews

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

4.95 out of 5 average rating, 265 reviews

A spacious family room features a dark leather sectional sofa arranged around a wooden coffee table. A large television unit is positioned against the wall, complemented by decorative elements. Soft lighting is provided by recessed ceiling lights and a standing lamp, creating a welcoming environment.

Guest suite in Lexington

Equestrian, Sports Fans, Bourbon Trailers

4.94 out of 5 average rating, 237 reviews

The exterior of a spacious carriage house is shown, featuring a stone facade and a grey roof. Three garage doors are visible, along with multiple windows framed in green shutters. A large tree provides shade to the front porch, which invites a sense of coming home.

Cottage in Shelbyville

Cozy Cottage on Firefly Farm

4.95 out of 5 average rating, 218 reviews

Luxury Retreat with Hot Tub

4.97 out of 5 average rating, 154 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

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.