Condo holiday rentals in Lexington

4.92 out of 5 average rating, 174 reviews

Graffiti Art Haus - Walk to Central Bank Arena

Industrial art haus just 3 blocks to Rupp Arena, a short walk to Gatton Park & only one block from Jefferson Street, with lots of dining & drinking options! Less than 1 mile to the Distillery District. Our guests will enjoy covered parking, luxury bedding, 2 smart TVs, a well-stocked kitchen & commercial laundry with sleeping arrangements for 4 people (1 king bed & 1 sofa bed). Whether you're in town for a concert, Keeneland, a wedding, graduation or work - this art haus is the ideal getaway!

A cozy living room features a comfortable sofa and a decorative armchair. Two floor lamps provide soft lighting, while a coffee table occupies the center. A large television is positioned on a stand, and natural light filters through a window with closed blinds.

4.93 out of 5 average rating, 208 reviews

*Bluegrass Getaway*

This apartment is a perfect location for catching a UK game, a weekend at Keeneland or a quick business trip. This apartment features an open concept kitchen and living area. The bedroom connects to a master bath with beautiful counter tops and fixtures. Simply pull the barn doors shut for privacy from the living area. Also features new stainless steel appliances, granite countertops, cultured marble shower, washer/dryer and convenient parking. 1.8 miles to Red Mile Casino, 2.5 miles to Rupp.

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.

4.94 out of 5 average rating, 267 reviews

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

A cozy sitting area features exposed brick walls and hardwood floors. A 55" Roku TV is mounted above an original but non-functioning fireplace. Two pull-out sleeper sofas and an armchair provide comfortable seating, complemented by a four-top dining table in the background.

5.0 out of 5 average rating, 32 reviews

Mary LeGrand's Penthouse - Downtown with parking

Mary LeGrand's Penthouse features two king bedrooms with ensuite full baths in a newly renovated and modernized 1860s Italianate home with original hardwood floors, a spacious private sipping porch, and more. Located in the childhood home of the University of Kentucky's first female valedictorian, Mary LeGrand Didlake, this 1550 square foot second story penthouse is just steps from everything Downtown Lexington has to offer, and is only a few feet off the campus of Transylvania University.

The bedroom features a spacious bed dressed in white linens, accented by vibrant green pillows. Tall green curtains frame two windows, allowing natural light to enhance the room. A large artwork adorns the wall above the bed, while a plush bench sits at the foot of the bed.

4.98 out of 5 average rating, 162 reviews

Great Location - 2 Mi. to Downtown - Rupp - UK

📍 Prime Location - Chevy Chase / Ashland Neighborhood 🚶 0.05 mi to restaurants, breweries & coffee shops 🌳 1 block to Woodland Park 🎓 1 mi to UK & Downtown 🏀 2 mi to Rupp Arena & Kroger Field ✈️ 5 mi to Blue Grass Airport Perfect for UK game days, concerts, bourbon tours, business travel, or a weekend getaway while enjoying one of Lexington's most walkable neighborhoods. 🏡 Renovated 1900s home with a Speakeasy & Flapper theme 📺 Smart TVs • 🛜 Fast Wi-Fi • 🚗 Plenty of parking

5.0 out of 5 average rating, 16 reviews

Thoroughbred Retreat Unit 803

Welcome to The Vine, Lexington’s premier destination for luxury living and unparalleled amenities. The Vine offers an exquisite blend of modern design and sophisticated comfort. Experience elevated living in this high-end, fully private condo with private parking and an unbeatable location. Whether you're in town for Keeneland, The University of Kentucky, Rupp Arena, or Lexington’s renowned restaurants and bourbon scene, this stunning retreat offers luxury, comfort, and convenience.

4.96 out of 5 average rating, 260 reviews

The FLAT at Bell Place - Downtown/Horse Park

Welcome to the historic Bell Court community, a close-knit neighborhood w/ lots of children & discerning families. Parties & other activities that do not meet the standards of the community will not be tolerated. Beautifully appointed 1st floor flat w/ stylish decor, a super comfortable bed & fast WIFI. * Rupp - 2 miles * Keeneland - 9 miles * Horse Park - 11 miles * STR Reg #15071157-1 - Max occupants 4 - Guests are prohibited from allowing more than Max occupancy *

Superhost

A modern living area features a comfortable gray sofa with colorful accent pillows, complemented by an elegant coffee table. An artistic mural adorns the wall behind, creating a vibrant focal point. Ambient lighting is provided by stylish floor lamps, enhancing the contemporary decor.

4.87 out of 5 average rating, 279 reviews

Lexington's Artistic Bunker / 1BR Downtown Condo

Lexington's Artistic Bunker is a space carefully crafted with amenities aplenty! Perfect for the traveling business, medical, or education professional, the guest visiting family/friends, or those experiencing the beauty of the Bluegrass, this modern condo is located in the heart of downtown Lexington. Featuring one bedroom, concrete floors, original murals, walk-in shower, and vaulted ceilings this high-end industrial condo will leave guests satisfied from every angle.

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.

4.96 out of 5 average rating, 27 reviews

HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator

Welcome to your stylish and spacious penthouse retreat in the heart of downtown Lexington! This newly built, modern suite with one king bed, 2 queen beds and sofa bed, offers everything you need for an unforgettable stay in the Bluegrass State. Whether you're here for a game at Rupp Arena, visit to the distilleries, a business trip, or to explore all that downtown Lexington has to offer, our luxurious penthouse is the perfect place to call your home away from home.

Superhost

Condo in Georgetown

5.0 out of 5 average rating, 3 reviews

The Luxe | Walk to Downtown|King Bed | 2BR Retreat

Welcome to The Luxe @ South Hamilton, a stylish 2-bedroom apartment in the heart of historic Downtown Georgetown. Walk to restaurants, coffee shops, boutiques, and Georgetown College. Enjoy a fully equipped kitchen, fast Wi-Fi, Smart TVs, in-unit washer and dryer, and a private outdoor patio perfect for relaxing. Just minutes from the Kentucky Horse Park, Toyota, Lexington, Keeneland, and the Bourbon Trail—ideal for work trips or weekend getaways.

4.95 out of 5 average rating, 105 reviews

The exterior of the Paradise Inn B&B showcases a charming three-story building with a vibrant yellow and red brick façade. Large windows are framed in white, allowing natural light to illuminate the interior. A sign for Paradise Cafe is prominently displayed at the entrance.

Condo in Paris

Paradise Inn B&B - Honeymoon Suite

The only B&B in Kentucky with an ‘Eiffel Tower’ view! Paradise Inn B&B is a unique penthouse suite atop "The World's Tallest Three Story Building" (from Ripley's Believe It or Not!) with exquisite oriental decor from the far East. The unbeatable hospitality is provided by your host and the owner, Lee Nguyen. This stay includes a $25 gift certificate for Paradise Cafe - Asian fusion and Pho restaurant located on the first floor.

4.9 out of 5 average rating, 188 reviews

💙The FLAT @ the LEX w/ Parking-Horse Park-Bourbon

Historic charm w/ modern comforts in this immaculate downtown first floor flat. Positioned at the entrance to Town Brach Distillery, this beautiful home is walkable to incredible restaurants and bars downtown Lexington - Don’t park in the front of the house, they will issue a ticket. * Rupp Arena 0.5 miles * Keeneland Racetrack 5.5 miles * Kentucky Horse Park 8 miles * STR Reg #15062369-2 - Maximum occupants 4

Popular amenities for Lexington condo rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Weekly condo rentals

4.92 out of 5 average rating, 25 reviews

A spacious living area features large windows allowing natural light to fill the room. A flat-screen television is mounted on the wall, and a comfortable sofa is positioned alongside two armchairs. A decorative area rug anchors the seating arrangement on the polished wooden floor.

Condo in Georgetown

The Oaks

A living room is presented with a large brown couch and a bright red armchair. A wooden coffee table sits in front of the couch, and a television is mounted on a stand opposite the seating. Soft lighting is provided by a lamp.

4.96 out of 5 average rating, 90 reviews

Gardenside Apartment: Private and Spacious

A cozy living room features exposed brick walls and a ceiling fan. A 60-inch television is mounted above a decorative fireplace. A coffee table is centered on a colorful area rug, and comfortable seating is arranged next to a window. A doorway leads to the kitchen.

4.82 out of 5 average rating, 220 reviews

Boho Bungalow

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.

4.98 out of 5 average rating, 62 reviews

Historic Downtown Condo

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.

5.0 out of 5 average rating, 26 reviews

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

A spacious living area is highlighted by a large television mounted above a white entertainment center, surrounded by various books. A cozy sitting arrangement includes a light-colored sofa and a brown recliner, with natural light filtering in through sheer drapes covering the expansive window.

5.0 out of 5 average rating, 27 reviews

Condo downtown Lexington

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

4.7 out of 5 average rating, 109 reviews

Capital City Condo #5

5.0 out of 5 average rating, 10 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

Pet-friendly condo rentals

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.

4.89 out of 5 average rating, 125 reviews

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

4.93 out of 5 average rating, 166 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

A welcoming living area features a spacious gray sofa adorned with decorative pillows, positioned on a soft area rug. The open layout reveals a modern kitchen in the background, with wooden cabinetry and appliances visible. Natural light streams in from the adjoining hallway.

4.89 out of 5 average rating, 354 reviews

*One Bedroom Apt | One Mile to Downtown Lex*

A spacious living area features a modern sectional sofa in gray, positioned near large windows allowing natural light. A rustic coffee table with a chessboard sits at the center, complemented by a sleek black refrigerator and wooden cabinetry in the kitchen area.

4.78 out of 5 average rating, 296 reviews

*Glamorous Downtown Apartment*

The bedroom features a spacious bed with a decorative bedspread, flanked by two bedside tables topped with lamps. Light grey walls and soft carpeting create a calming environment, while decorative wall elements enhance the overall appeal.

4.92 out of 5 average rating, 181 reviews

*Private Apartment with Balcony | W/D inside apt*

A cozy living area is visible, featuring a dark sofa flanked by two tall lamps on stylish stands. A coffee table is centered in front of the sofa, with a textured area rug beneath. A television is mounted on the wall, and a window allows natural light to fill the space.

4.93 out of 5 average rating, 226 reviews

*New Cozy Apartment| 2 miles to downtown Lex*

4.87 out of 5 average rating, 113 reviews

175 Lex-Walkable Downtown Lexington Condo

An open living area is featured, showcasing a sectional sofa and a round dining table with chairs. The kitchen, equipped with modern appliances, includes a breakfast bar with tall stools. Natural light fills the space through large windows, creating a bright atmosphere.

4.76 out of 5 average rating, 122 reviews

175 LEX - Spacious Two Bedroom Downtown Lexington

Private condo rentals

5.0 out of 5 average rating, 11 reviews

Teal & Barrel Unit 411

Superhost

5.0 out of 5 average rating, 4 reviews

Rye'd Away Unit 505

5.0 out of 5 average rating, 10 reviews

The Champion's Suite Unit 809

A modern living space is presented with a light-colored sectional sofa and neutral decor. Natural light enters through large windows, highlighting the open kitchen area with bar seating. A ceiling fan provides added comfort, while a tastefully arranged area rug adds texture to the floor.

4.89 out of 5 average rating, 100 reviews

175 LEX - Bon Voyage Condo

A modern living room features a large sectional sofa and a circular coffee table, complemented by hardwood flooring. Two pieces of artwork adorn the walls, and a round mirror reflects natural light. A large window provides views of the cityscape.

4.92 out of 5 average rating, 139 reviews

Bourbon Condo Downtown Lexington

A bright bedroom area features large windows that offer views of Downtown Lexington's skyline. A spacious bed is positioned against a wall, and light-colored curtains frame the windows, allowing natural light to fill the room.

4.82 out of 5 average rating, 151 reviews

175 LEX - Stunning Downtown Views on Main Street!

The bedroom features a plush black bed with a white textured coverlet and striped accent pillows. Two modern bedside lamps are positioned on either side. Three decorative wall pieces add visual interest above the headboard, while a large window allows natural light to fill the room.

4.87 out of 5 average rating, 45 reviews

Lex In The City - Downtown Condo

The kitchen showcases modern appliances, including a stainless steel refrigerator and stove. Dark cabinetry contrasts with light quartz countertops. A spacious island with a sink provides additional prep space. A hallway leads to an entryway, reflecting a seamless open layout.