Vacation rentals in Lexington

4.99 out of 5 average rating, 171 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)

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, 364 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

4.99 out of 5 average rating, 434 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 elm 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 bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

The bedroom features a spacious bed with multiple pillows and a cozy blanket. Light-colored walls enhance the bright ambiance, complemented by two windows on either side. A decorative wall hanging adds character, while bedside tables hold books and lamps for a welcoming touch.

4.81 out of 5 average rating, 268 reviews

The Loft @ West Second

Book the 2nd floor Loft of this beautiful historic house. Located on West 2nd St. with easy on street parking. Walkable to downtown off ofJefferson St with shops and restaurants. Hop skip or jump to the new Gatton Park. Easy walk to Rupp Arena, The Civic Center, Triangle Park and all that Downtown Lexington has to offer. Sweet access to The Bourbon Trail! The University of Kentucky is less than 2 miles away, KY Horse Park, The Bluegrass Airport, and Keeneland are all within a 15 minute drive.

4.93 out of 5 average rating, 808 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.

Home in Woodward Heights

Restored charm! Walk to Rupp. Easy Keeneland drive

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert or sporting event at nearby Rupp Arena (5 minute walk), watch the horse races at Keeneland (10 minute drive down the road), tour the bourbon distillery right around the corner, or explore the unique offerings of downtown Lexington. Stay in the heart of it all!

4.99 out of 5 average rating, 235 reviews

The open living area features a high ceiling with wooden beams, a comfortable leather sofa, and armchair. A dining table is set for four, complementing the rustic décor. A staircase leads to the loft, while glimpses of the kitchen are visible in the background.

Cabin in Lawrenceburg

Relax in the hot tub w/a view of the River!

Welcome to the Kentucky River Bourbon Cabin! We are back open after the 4/25 flood! Relax and rejuvenate in this cozy cabin nestled in a wooded setting & on the edge of the Kentucky River! Here you will find peace and serenity in nature with an upfront view of the water. Secluded and private yet still close to stores, restaurants and many tourist attractions such as major distilleries and wineries. Four Roses, Wild Turkey, Woodford Reserve and Buffalo Trace are just a short drive away.

The kitchen features smooth beige cabinetry and granite countertops, complemented by a stylish tile backsplash. Modern stainless steel appliances, including a refrigerator, oven, and microwave, are present. Ample storage is provided with numerous cabinets, creating a functional cooking space.

4.95 out of 5 average rating, 174 reviews

Southern Hospitality! Best location close to UK!

This home has been completely renovated with truly flawless finishes. Approximately 1 mile from all hospitals; UK, Central Baptist, St.Joseph. New kitchen and appliances. Very convenient location to Keeneland, Shopping, and Restaurants. Extremely clean and comfortable living spaces. The living and bed rooms have been equiped with Tv’s. WiFi is included. The shower even has a Bluetooth fan for playing music in the shower. I’ve provided everything to make your trip as enjoyable as possible.

Apartment in Woodward Heights

An interior space is shown with a spacious bed in the foreground. A glass garage door opens to a private patio area. Wood paneling adorns the walls, complemented by a television and storage shelves. Natural light fills the room, enhancing a sense of openness.

4.94 out of 5 average rating, 347 reviews

Enjoy Downtown Lex from your Private Deck

Walkable to downtown, Rupp/Convention Center, Town Branch Distillery & less than 1 mi to UK student center. 12 min drive to Keeneland, 19 min to horse park. Sleeps 2-3 with 1 queen size bed and a couch bed. Equipped with basic kitchen amenities, all new appliances, washer/dryer, 2 Smart TVs & WIFI. Bedroom features a glass garage door that opens to a private patio. This apartment is located in a brand new building with free parking on premises. Energy efficient, simple, center of it all!

Superhost

A bright living area features large windows offering views of the surrounding cityscape. A circular dining table with white chairs is positioned next to a modern couch. The room is complemented by a ceiling fan and stylish light fixtures, enhancing the contemporary atmosphere.

Condo in Lexington

4.81 out of 5 average rating, 151 reviews

175 LEX - Walkable Downtown Condo & Stunning View!

Offering unparalleled views of Downtown Lexington, immerse yourself into living like a local at 175 LEX! Condo 501 has recently been renovated featuring all the modern-day amenities a guest would desire when visiting Central KY. Residing on the 5th floor, this condo-hotel features one bedroom with a queen-sized bed, living room with sleeper sofa, full kitchen w/ quartz and private washer/dryer. Walkable to Rupp Arena, local restaurants like Carson's, coffee shops, retail shops, & more!

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

4.98 out of 5 average rating, 497 reviews

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

4.93 out of 5 average rating, 246 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

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but 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

4.98 out of 5 average rating, 179 reviews

A classic bungalow features a welcoming front porch, framed by two trees and a well-maintained lawn. The home is set back from the sidewalk, showcasing a path leading to the entrance. A spacious fenced yard is visible to the side, providing a private outdoor space.

Bungalow in Kenwick

Cozy Kenwick Bungalow in the Heart of Lexington

Welcome to your home away from home in Kenwick, one of Lexington's favorite neighborhoods! This classic bungalow has 3 bedrooms (queen beds in 2 rooms and 2 twin beds in another room) plus a bright basement room with a sleeper sofa. Sit outside on the covered front porch or sit on the back deck and enjoy the fenced in yard. Kenwick is centrally located and is an easy drive to many popular destinations including downtown, UK, the bourbon trail, the Kentucky Horse Park, and Keeneland.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Lexington vacation rentals

Laptop-friendly workspace

Pet-friendly vacation rentals in Lexington

4.94 out of 5 average rating, 212 reviews

The exterior of a two-story brick building is displayed, featuring a welcoming porch with white railings. Lush green trees frame the entrance, and a path leads to the front door. The property exhibits a blend of classic architecture and natural surroundings.

Apartment in Ashland

Canopy of trees

Superhost

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.

4.84 out of 5 average rating, 171 reviews

*Luxury One Bedroom Apt| Downtown Lexington*

4.93 out of 5 average rating, 227 reviews

A spacious living area is highlighted, featuring a brown couch and a circular coffee table atop a patterned rug. Large windows allow ample light, while a ceiling fan enhances airflow. A dining table and kitchen area are visible in the background, promoting an open layout.

Townhouse in Lexington

Mulberry Hill

4.88 out of 5 average rating, 128 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

A spacious jacuzzi is featured in a serene outdoor setting, surrounded by lush greenery and tall trees. Sunlight filters through the leaves, creating a warm atmosphere. The inviting waters reflect the sky, providing a relaxing escape just outside the house.

4.9 out of 5 average rating, 174 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

A compact kitchen showcasing wooden cabinets and granite countertops. Stainless steel appliances include a gas range, microwave, and refrigerator. A coffee maker sits on the counter. A small wooden dining table with black chairs is positioned beside the door, which features a natural wood finish.

4.89 out of 5 average rating, 254 reviews

Clean Private Studio w/Full Kitchen (Wildcat Den)

4.91 out of 5 average rating, 455 reviews

A living room area is featured, showcasing a black couch adorned with cushions. A trundle bed is positioned next to the couch, set with a white bed linen and a pillow. A round side table holds a vase with colorful flowers, while a TV is mounted on the wall.

Farm stay in Versailles

Bluegrass Country Cottage

Superhost

The kitchen features white cabinetry with modern hardware, accented by a dark brick backsplash. Stainless steel appliances include a microwave and a gas stove. A granite countertop runs along the length, complemented by kitchen utensils and a small bottle of wine on the counter.

4.75 out of 5 average rating, 239 reviews

Third Street Getaway in Lexington KY.

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House rentals in Lexington

4.93 out of 5 average rating, 281 reviews

A spacious bedroom features a comfortable bed dressed in soft bedding. Natural light is provided by a window, and a ceiling fan offers airflow. A wooden dresser and two nightstands add functionality, while tasteful decor pieces enhance the inviting ambiance.

Home in Nicholasville

Cali King beds w/ Koi pond Oasis. 15 min from LEX

A cozy living area is highlighted by a fireplace beneath a mounted television. A light green sofa and a beige couch are arranged around a circular coffee table. Natural light filters through the large arched window, complemented by indoor plants placed thoughtfully in the corner.

4.95 out of 5 average rating, 107 reviews

Cottage Circle Home

A charming brick home with a gabled roof is framed by lush green trees and landscaped garden beds. A stone pathway leads to the front porch, where two white chairs invite relaxation. The welcoming facade features multiple windows allowing natural light.

4.95 out of 5 average rating, 252 reviews

3BR-4 Beds-2BA close to UK/Chevy Chase/Downtown

A spiral slide in vibrant burgundy extends from a wooden ceiling to the floor, creating a playful focal point in the space. Natural light filters through windows, illuminating the smooth wood flooring and surrounding area, which includes modern appliances and a stylish chair.

4.95 out of 5 average rating, 113 reviews

Maryland Luxury Downtown Manor

A cozy living area showcases a leather couch and a plush chair, inviting relaxation. A wooden coffee table sits in the center, while natural light filters through the windows with blinds. A minimalist artwork hangs on the green accent wall, enhancing the overall aesthetic.

4.87 out of 5 average rating, 153 reviews

El Retro- Mid Century Ranch near Horse Park & Rupp

The front entrance of the home features a welcoming porch with steps leading up to a dark iron railing. Lush greenery and flower pots are seen along the pathway, while a maple tree provides shade to the area, enhancing the home’s curb appeal.

4.92 out of 5 average rating, 101 reviews

University of KY/hospital area-#15082674-1

The living room features vaulted ceilings and an open layout. A sectional sofa and a reclining chair offer comfortable seating, while a coffee table sits centrally. Light hardwood flooring and soft wall decor contribute to a bright and airy ambiance. A large TV is mounted on a nearby wall.

4.99 out of 5 average rating, 118 reviews

Newly renovated upscale house with high ceilings

A welcoming front porch features a solid door with an address number visible. A small, potted evergreen plant stands next to the door. A black chair with a red cushion is positioned nearby, alongside a geometric decorative table. The porch floor is finished in dark wood.

4.94 out of 5 average rating, 429 reviews

Big Rock Cottage

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Pet-friendly house rentals Lexington

A charming brick home is framed by lush greenery, featuring a distinctive peaked roof. A well-maintained front yard includes neatly trimmed shrubs. Stairs lead to a welcoming entryway with a decorative wrought-iron door, while large windows allow natural light to fill the interior.

4.95 out of 5 average rating, 104 reviews

Lexington's Commonwealth Cottage STR:15070620-1

4.98 out of 5 average rating, 147 reviews

A bright living area features a light-colored sofa and two beige armchairs arranged around a glass coffee table. Natural light enters through two large windows, complemented by white curtains. A green front door adds a pop of color to the welcoming space.

Home in Kenwick

The Rosewood Cottage of Lexington I Elegant & Cozy

A modern living area features a comfortable brown sofa with decorative pillows and a round coffee table. Large windows with sheer curtains allow natural light to fill the space. A flat-screen TV is mounted above a white fireplace, and a stylish wicker chair adds additional seating.

4.94 out of 5 average rating, 102 reviews

3 bed (2kings) 2.5 bath spacious remodeled home

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.

4.97 out of 5 average rating, 126 reviews

Bluegrass Fall FunZone! Pool! Hottub! GameRm!

A charming exterior of a single-story home is displayed, featuring dark blue siding and a welcoming front porch. Neatly trimmed shrubs frame the entrance, and an American flag hangs by the door. Sunlight bathes the scene, highlighting the surrounding greenery.

4.99 out of 5 average rating, 162 reviews

Cheerful and Cozy in the Heart of Chevy Chase!

4.98 out of 5 average rating, 243 reviews

A spacious brick home with a welcoming front porch features white railings and steps leading up to a mint green door. Lush greenery and well-maintained landscaping create a charming entrance, complemented by a bright blue sky above.

Home in Mentelle

Bell Ct-133 N Ashland Ave-Horse Park-Bourbon Trail

The exterior of the updated bungalow is presented, showcasing a wide front porch with a welcoming entrance. Lush greenery surrounds the steps, and the house features white brick and a prominent wooden front door, creating an inviting first impression.

4.93 out of 5 average rating, 176 reviews

Hot Tub | Walk to Downtown | Patio | Fire Pit | Ga