Holiday rentals with a patio in Frankfort

A dining area features a round wooden table set with glassware and green accents. A striking mural of bourbon barrels lines one wall, illuminated by a modern pendant light, while a doorway leads to other spaces in the home.

5 out of 5 average rating, 104 reviews

*Long Pour: Your Luxury Downtown Bourbon Home*

Welcome to bourbon heaven. Really. 🥃 Long Pour is located in the heart of Frankfort and bourbon country, - walking distances from Buffalo Trace, downtown restaurants, bars, and historic neighborhoods. Our place is a luxury home away from home featuring two bedrooms, an iconic shower, free parking, and not to mention the bourbon features all throughout the home. No matter your reason for visiting Frankfort, this home is the perfect getaway to enjoy the best of Kentucky. Can't wait to host y'all!

4.99 out of 5 average rating, 186 reviews

The cabin exterior is nestled within a wooded landscape, showcasing a wooden facade. A welcoming porch is framed by two Adirondack chairs, with stepping stones leading toward the entrance. Twinkling lights hang across the trees, enhancing the tranquil evening ambiance.

Cabin in Lawrenceburg

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

5 out of 5 average rating, 108 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

Bourbon Trail Cabin~Enjoy Christmas decor in Dec!

🌲FOR CHRISTMAS- home is transformed into cozy holiday cabin retreat! A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plenty of fun on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

4.98 out of 5 average rating, 161 reviews

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

Home in Lawrenceburg

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

4.99 out of 5 average rating, 136 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, 181 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 game room is presented with a pool table at its center, surrounded by wooden flooring. A vintage slot machine and an air hockey table are visible against a wall. Natural light enters through a window covered by sheer curtains, and a flat-screen TV is mounted on an adjacent wall.

4.88 out of 5 average rating, 110 reviews

Bourbon Trail Downtown Frankfort w/Game Room

Close to several Bourbon Distilleries, Buffalo Trace, Keeneland, and breweries. Home has kitchen, dining room, living room, game room, bathrooms, laundry, outdoor space, and private bedrooms. The bedrooms have a tv, king bed, dresser & sofa. Futon and kids table located in one bedroom. Downtown Frankfort is a scenic 20 minute walk along the river and hosts an active scene of local restaurants, bars, shops & history. This house has everything you need for a fun enjoyable stay! #BourbonTrail

4.99 out of 5 average rating, 243 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

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.

4.94 out of 5 average rating, 190 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.

4.99 out of 5 average rating, 456 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!

4.94 out of 5 average rating, 299 reviews

A spacious glamping tent is set among vibrant greenery, featuring a conical roof and large entrance. Natural light filters through the trees, casting soft shadows on the wooden deck. The scene captures a peaceful ambiance, inviting guests to relax in nature.

Treehouse in Georgetown

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

4.98 out of 5 average rating, 196 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

Experience the warmth and charm of The Loft your top-rated fall retreat just 8 minutes from downtown. Stroll to the Capitol, see the autumn sights, and take in Horse Country nearby. Snuggle into a cozy bed, curl up on the couch, and enjoy modern touches in your private second-floor hideaway. With parking at the door and a hygge-inspired vibe, it’s perfect for crisp days and cozy nights. Just minutes from 13 distilleries, The Loft is your ideal base for a stylish Bourbon Trail escape.

Popular amenities for Frankfort Holiday Houses with Outdoor Verandahs

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

5 out of 5 average rating, 62 reviews

A spacious living area is highlighted by a light-colored sofa adorned with decorative pillows. Artwork featuring playful horse designs decorates the gray walls. A glass coffee table sits atop a patterned rug, and a TV is positioned on a white media console, creating a cozy atmosphere.

Apartment in Gratz Park

Centrally Located Lex Apartment!

4.98 out of 5 average rating, 165 reviews

The living area features exposed wooden beams and a spacious sectional sofa facing a large television. A round side table and a lamp provide soft lighting. A set of double doors leads to a bright seating area with large windows, enhancing the open feel.

Apartment in Lexington

LUX W 6th Penthouse w/ Private Balcony - King Bed

5 out of 5 average rating, 22 reviews

A spacious living room features two comfortable sofas and a coffee table, arranged to encourage conversation. Natural light flows in through large windows adorned with shutters. A wall-mounted television and bookshelves filled with books add functionality and warmth to the space.

Apartment in Frankfort

Duvall's Downtown Guest Suite

4.8 out of 5 average rating, 5 reviews

An open living area features a comfortable sofa and armchair, with a rustic coffee table positioned centrally. A large wall-mounted TV is visible, alongside a stylish kitchen with wooden cabinetry and modern appliances. Natural light streams through windows, highlighting the warm wood floors and decorative area rug.

Apartment in Frankfort

Close to Buffalo Trace/ 2 Bedroom/ Newly Renovated

4.98 out of 5 average rating, 64 reviews

A spacious room features a plush green and purple color scheme. A comfortable sofa and an accent chair provide seating. A coffee table holds magazines, while a vibrant equestrian-themed artwork adorns the wall. Natural light filters through the window with blinds, enhancing the inviting space.

Apartment in Versailles

Morgan Street Apartment

4.93 out of 5 average rating, 41 reviews

A living area features a brown leather couch positioned on a light blue area rug, with a dark ottoman in front. Natural light enters through a nearby window. A white bookshelf displays a selection of items, while a dining area is visible in the background.

Apartment in Lexington

CentraLex Flat

4.82 out of 5 average rating, 72 reviews

Apartment in Frankfort

Pappy's Man Cave- 300yds from BT

4.8 out of 5 average rating, 64 reviews

An open-concept living area features a light blue accent wall, a comfortable gray sofa with decorative pillows, and a wooden coffee table positioned on tiled flooring. Natural light filters through the window, enhanced by surrounding decor and a ceiling fan above.

Apartment in Wilmore

Wilmore Cozy Corner Reg. #9575

Holiday House Rentals with a Verandah

The newly renovated farmhouse features a white exterior with a red metal roof. A covered porch extends across the front, with a wooden bench providing a place to sit. The surrounding yard is spacious and grassy, framed by trees in the background.

4.9 out of 5 average rating, 129 reviews

Morrow House-Newly Renovated Farmhouse 3 bedrooms

4.83 out of 5 average rating, 109 reviews

A charming backyard features a spacious patio area with a BBQ grill and seating under a sunshade. Lush green grass surrounds the patio, enhancing the outdoor setting. The home is painted in a deep blue, complemented by a colorful sunset creating a serene backdrop.

Home in Lawrenceburg

Bourbon Trail/8 mins to distilleries/Fenced Yard

A new six-seater hot tub is showcased, illuminated by soft blue lights. A small platter rests on the edge, accompanied by two wine glasses. In the background, warm light spills from an inviting seating area visible through the glass doors.

4.98 out of 5 average rating, 57 reviews

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

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.

4.95 out of 5 average rating, 95 reviews

Whiskey Woods: Newly Remodeled w/ HOT TUB!

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, 93 reviews

Backyard Bourbon Retreat

5 out of 5 average rating, 111 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

4.86 out of 5 average rating, 56 reviews

Kentucky Bluegrass Retreat - Large Deck - lvl 2 EV

A charming stone home is surrounded by lush greenery and vibrant flowering shrubs. A stone pathway leads to the front door, framed by a variety of trees that provide shade and tranquility. Sunlight filters through the leaves, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 16 reviews

Bourbon Trail-Hot tub-Riverview-2.5miles BuffaloTr

Holiday condos with a patio

A comfortable brown sofa is positioned against a light-colored wall, complemented by two decorative pillows with orange fringe. A wooden side table with a slightly weathered finish is placed nearby. The floor is covered with a patterned area rug, adding a touch of warmth to the space.

Condo in Frankfort

4.68 out of 5 average rating, 96 reviews

Capital City Condo #5

A dark gray sofa with decorative pillows sits against a light wall. A round wall clock is positioned above the sofa, displaying an elegant design. A patterned area rug in muted tones lies beneath the furniture, complementing the overall decor.

Condo in Frankfort

4.74 out of 5 average rating, 115 reviews

Capital City Condo #2

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

4.91 out of 5 average rating, 106 reviews

A spacious living room featuring a light-colored sectional sofa with ample seating, complemented by a dark wood coffee table. Large windows allow natural light to fill the space, framed by navy blue curtains. A ceiling fan enhances airflow in this modern area.

Condo in Lexington

Penthouse @ 175 LEX -Walk to Rupp Arena on Main St

5 out of 5 average rating, 9 reviews

A modern living space is highlighted by a comfortable leather armchair and a round glass coffee table. A mounted television and a linear electric fireplace are positioned against a feature wall. Natural light enters through a window, illuminating the dining table in the background.

Condo in Harrodsburg

Salt River Bed and Barn

4.8 out of 5 average rating, 5 reviews

A two-story building is shown, featuring a covered porch that wraps around the front. The exterior walls are painted white, contrasted by black trim. A large yard and open fields surround the property, with clear blue skies overhead.

Condo in New Castle

The Bunker

Condo in Historic South Hill

A modern kitchen features a central island with a light-colored countertop, surrounded by four wooden bar stools. Stainless steel appliances and sleek cabinetry are visible, complemented by pendant lighting above. The space is designed with a mix of tile and hardwood flooring.

4.95 out of 5 average rating, 20 reviews

HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator