Holiday rentals with outdoor seating in Frankfort

The exterior of a brick home is shown, featuring a welcoming front door in a light teal shade. Surrounding landscaping includes neatly trimmed shrubs and flowering plants, with a concrete pathway leading to the entrance. A well-maintained lawn stretches out in front.

4.99 out of 5 average rating, 104 reviews

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

5 out of 5 average rating, 200 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 wooden shelf displays six barrels, each marked with labels and handwritten notes, reflecting a bourbon-tasting theme. Bar stools are positioned in front of the shelf, providing seating for guests in a welcoming space.

5 out of 5 average rating, 100 reviews

Van Winkle's Secret/Speakeasy (Hidden Room)

If you like bourbon, you will LOVE this place. Perfect for families, friends, bourbon hunters, and bachelor/ettes! You will find a hidden speakeasy lounge if you look hard enough! There are 16 distilleries within 35 min, including Buffalo Trace (7 min). Wineries, breweries, bars, restaurants, and entertainment all within Frankfort! Featuring 3 king beds, a pullout couch, 2 full and 2 half baths. Gather on the patio or out by the fire. The large fenced in yard will give you plenty of privacy.

4.98 out of 5 average rating, 638 reviews

Cabin in Lawrenceburg

Bourbon Trail Cabin on the Farm

Recognized as Airbnb’s “2021 Top New Airbnb in Kentucky,” this cozy farm cabin overlooks rolling fields on a working cattle farm. Meet and feed cows, goats, a pig, and our beloved donkey Otis! Inside, enjoy hand-crafted charm with barn wood walls, full bath with bourbon barrel sink, king bed, sleeper sofa, and custom kitchenette. Connect with nature in the large outdoor pavilion with a stone fireplace. Located in the heart of the Bourbon Trail, close to Wild Turkey, Four Roses, & Buffalo Trace!

4.94 out of 5 average rating, 247 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.

Guesthouse in Frankfort

The Carriage - Quaint Haven steps to the Capitol

Welcome spring at a chic Parisian-style hideaway in Historic Frankfort, where charm and comfort meet in every detail. Just minutes from 13 iconic distilleries and the KY Capitol, this cozy retreat is perfectly placed for bourbon tastings, local history, and leisurely city strolls. Inside, enjoy fast Wi-Fi, a smart TV, full kitchen, private entry, and free parking. Rest deeply in a plush queen bed, then sip coffee or wine on the bistro deck as fresh spring days fade into relaxed, perfect nights.

A modern kitchen is showcased, featuring stainless steel appliances and white cabinetry. The spacious marble countertop is complemented by decorative elements, including teal accents. A cutting board rests on the counter while colorful artwork adorns the wall, adding a touch of vibrancy to the space.

4.95 out of 5 average rating, 240 reviews

Lil Bit O' History on Main- Historic Downtown!

Built in 1867, with original deed of 1813, this beautiful piece of Frankfort's history has been fully restored! This cozy shotgun home offers magnificent views of the State Capital in front and of the Old Capital from the side! Located along the Bourbon Trail, it offers a short walk to BOM, local breweries, downtown coffee at Kentucky Coffee Tree, and all the shops of Broadway. The History Center is close, as is The Kentucky Military Museum. Buffalo Trace and Castle and Key are minutes away.

A welcoming view of The Spencer cottage is presented, showcasing lush greenery and carefully tended landscaping. A sign is positioned in the foreground, displaying the name of the property. The brick exterior of the cottage is framed by trees, enhancing its charming appeal.

4.9 out of 5 average rating, 132 reviews

Frankfort’s Capitol view cottage

Frankfort's Capitol View Cottage Named for architect Spencer Cryer, the Spencer offers a unique charm with the comforts of home on your central Kentucky travels. An off the beaten path yet still downtown cottage with a seasonal view of the Capitol, the home offers both inside and outside amenities. Steps from the Capitol grounds and 20 miles to Lexington 50 miles to Louisville and within an hour drive of at least 10 distilleries on the Bourbon Trail including Buffalo Trace a local favorite!

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, 215 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.

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.

4.88 out of 5 average rating, 113 reviews

Capitol Walk/7min to Buffalo Trace

Enriched with history & tradition is where you will find Capitol Walk. 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!

A spacious living area features a plush blue sofa and two vibrant yellow chairs. A flat-screen TV is positioned on a white console. Natural light filters through multiple windows, illuminating a decorative area rug placed on the warm wood flooring.

4.96 out of 5 average rating, 113 reviews

Whiskey Woods: Newly Remodeled w/ HOT TUB!

Discover Whiskey Woods in picturesque Frankfort, KY! This 3-bed, 2-bath retreat on 3.6 acres offers modern amenities. Enjoy open-concept living, a fully equipped kitchen, and outdoor dining. Explore the lush property with grill. Sleep in plush beds, including a king-sized Whiskey Suite. Stay connected with Wi-Fi, laundry, and parking. Only 1.4 miles from Castle and Key Distillery, and 4.9 miles from Woodford Reserve. Minutes from downtown attractions. Book your Frankfort getaway today!

4.98 out of 5 average rating, 135 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.

Guesthouse 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.

4.99 out of 5 average rating, 103 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.

Popular amenities for outdoor seating rentals in Frankfort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 103 reviews

The master bedroom features a spacious bed with a dark blue bedspread, complemented by light-colored pillows. Exposed wooden beams add a rustic touch to the ceiling. A large area rug sits beneath the bed, enhancing the room's warmth. A framed artwork is displayed on the wall.

Home in Georgetown

Springside Equine Getaway

A living area features a dark leather sectional sofa and a patterned accent chair, providing ample seating options. A low coffee table sits on a colorful area rug, while natural light fills the space through nearby windows. A door leads to the exterior.

4.99 out of 5 average rating, 172 reviews

Horse Central-Be our Guest!

5 out of 5 average rating, 119 reviews

The home is nestled amidst a backdrop of gently rolling hills, framed by trees showcasing autumn foliage. A welcoming front porch is visible, accompanied by a small staircase leading to the entrance. Large windows allow natural light to filter into the living space.

Home in Versailles

Birdsong Valley on Bourbon Trail

4.94 out of 5 average rating, 179 reviews

The cottage's exterior features a charming red facade with a steep roof, framed by lush greenery. A pathway leads to the welcoming front door, flanked by two tall shrubs. The landscaped garden includes various plants and decorative stones, creating an inviting entrance.

Home in Harrodsburg

The Betsy Sweat Cottage.

4.98 out of 5 average rating, 453 reviews

Distillery District Diamond-pet friendly

Superhost

A modern living room features a dark sectional sofa accompanied by two light-colored armchairs. A natural woven rug covers the floor, and a small wooden coffee table sits in the center. Greenery from a potted plant adds a touch of nature, complemented by soft lighting from a floor lamp.

Home in Lawrenceburg

4.88 out of 5 average rating, 172 reviews

The Homestead| Downtown| Near Bourbon Trail

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.

4.95 out of 5 average rating, 380 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

A close-up view captures the bubbling surface of a hot jacuzzi, steam rising gently into the air under a bright sun. The light reflects off the water, creating a serene atmosphere, while trees in the background provide a natural setting.

4.92 out of 5 average rating, 214 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

Apartment rentals with outdoor seating

4.85 out of 5 average rating, 149 reviews

A spacious living area features a dark sectional sofa and a round coffee table set on a decorative area rug. Natural light floods through the large bay windows with white drapes, illuminating the contrasting hardwood flooring and the cozy dining set nearby.

Apartment in Georgetown

Man O'War @ The HoM- KY Horse Park, Ark, Historic

4.99 out of 5 average rating, 146 reviews

A vibrant seating area features a plush red sofa adorned with decorative pillows. A light marble side table sits nearby, complemented by an intricate metal screen and lush greenery. Warm lighting from hanging fixtures enhances the inviting atmosphere of the space.

Apartment in Lexington

Swanky Boho - Downtown

Apartment in Meadowthrope

A cozy living area features a striped sofa and two armchairs, creating a comfortable seating arrangement. Two lamps provide soft lighting, while a wooden side table holds a small plant. The hardwood floor is complemented by a large area rug, enhancing the warm atmosphere.

4.95 out of 5 average rating, 156 reviews

Nonie's Abode

4.89 out of 5 average rating, 169 reviews

A wooden railing overlooks a serene river, with trees lining the opposite bank. A cozy plaid blanket drapes over the railing, alongside a glass decanter and two glasses, capturing the golden hues of a sunset.

Apartment in Winchester

Riverview 2 … enjoy the view !

4.86 out of 5 average rating, 214 reviews

The kitchen features modern white cabinetry and stainless-steel appliances, including a microwave and refrigerator. A double sink is positioned beneath a wall art piece, and a small decorative plant adds a touch of greenery to the countertop. Light reflects off the surfaces, enhancing the clean look.

Apartment in Lexington

*Luxury One Bedroom Apt| Downtown Lexington*

4.87 out of 5 average rating, 383 reviews

A spacious living room is presented with a comfortable sectional sofa adorned with patterned cushions. A round glass coffee table is situated in the center, featuring decorative elements. Warm light is emitted from two lamps, illuminating the inviting space, complemented by framed artwork on the wall.

Apartment in Frankfort

Ky Bourbon and Horses-300YD from BT Distillery

4.91 out of 5 average rating, 101 reviews

An aerial view captures a two-story house with a dark roof and a white exterior, positioned next to a well-maintained lawn. A concrete driveway leads to the entrance, with paths of grass lining the edges. Surrounding buildings and greenery are also visible.

Apartment in Lexington

Victorian Apt Downtown Lexington

Apartment in Woodward Heights

The living area features a comfortable gray sofa paired with two orange accent chairs. A dark coffee table sits in front, complemented by a large, colorful artwork on the wall. A flat-screen TV is positioned on a wooden stand, with plants adding a natural touch.

4.98 out of 5 average rating, 348 reviews

Downtown Apartment in Victorian Home

Apartment rentals with outdoor seating

4.88 out of 5 average rating, 130 reviews

Condo in Shelbyville

Cozy condo, work, family, friends

4.98 out of 5 average rating, 53 reviews

A welcoming bedroom features a spacious bed layered with neutral and earthy-toned bedding. A round mirror reflects natural light from the window, enhancing the room's brightness. A comfortable chair and a sleek dresser are positioned beside the bed, while an area rug adds warmth to the hardwood floor.

Condo in Lexington

Historic Downtown Condo

Condo in Historic South Hill

An open living area features wooden ceilings, large windows dressed with patterned curtains, and stylish seating options. A mix of modern and vintage furniture creates a cozy space, complemented by decorative rugs and a dining area adorned with a chandelier.

5 out of 5 average rating, 20 reviews

The Big Blue Wave - 2-Bedroom Condo by Rupp Arena

4.95 out of 5 average rating, 249 reviews

An open living area features large glass doors that provide views of the greenery outside. Industrial elements, such as exposed beams and metal accents, complement a cozy seating arrangement with a sectional sofa and wooden coffee table. A dining table with bar stools is visible in the background.

Condo in Lexington

Top Shelf the only Airbnb in KY above a Distillery

4.93 out of 5 average rating, 163 reviews

A living area features two dark couches adorned with decorative pillows, situated around a wooden coffee table. Soft lighting is provided by two table lamps. A small desk with an office chair is positioned in the corner, while a patterned rug anchors the space.

Condo in Frankfort

Bourbon Trail R&R

Superhost

Condo in Historic South Hill

Rye'd Away Unit 505

4.87 out of 5 average rating, 60 reviews

The living room features a light-colored sofa and armchair, complemented by wooden side tables. A large wall-mounted TV and a ceiling fan are visible, along with a plush area rug. Natural light comes from the door leading to an outdoor space.

Condo in Crestwood

Luxury Apartment/Near Louisville/EV Charger