Condo vacation rentals in Lexington

A gracefully curved staircase features wood steps with a polished handrail. The balustrade is adorned with white spindles and rich wood detailing, set against soft blue walls. Natural light illuminates the space, highlighting the original hardwood floor at the base.

5 out of 5 average rating, 18 reviews

Mary LeGrand's Penthouse - Downtown

Mary Legrand's Penthouse features two king bedrooms with ensuite full baths in a newly renovated and modernized 1860s Italianate home featuring 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.

5 out of 5 average rating, 12 reviews

Condo in Nicholasville

Townhouse #1 @ The Corner House

Spacious & modern 2 bedroom townhouse with 1 1/2 baths, fully furnished kitchen, washer & dryer, living room, free wireless internet and cable tv. Each bedroom has a queen-sized bed and both bedrooms are located on the second floor with a full bath. Beautiful view off of the back deck. Also has a grill & private driveway. Safe neighborhood. This house is within walking distance of many restaurants and stores. It is 2 blocks from Main St. Why stay in a hotel room when you can have a whole house?

A tree-lined entrance leads into the property, featuring a paved driveway that extends beyond a wooden fence. Lush greenery and tall trees create a natural canopy, providing a serene backdrop to the welcoming approach.

4.89 out of 5 average rating, 288 reviews

*New Downtown Apartment*

One Bedroom Apartment in Downtown Lexington. Enjoy a walk on the Legacy Trail or grab a bite to eat at one of the many restaurants in Downtown Lexington. Our One Bedroom Apartment is conveniently located near University of Kentucky, Transylvania, Legacy Trail, Restaurants, Fine Dining & Nightlife. Walkable to nearby yoga studio, Lyric Theatre, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Martine's Pastry next door is perfect for your morning wake up. Approximately, 5 miles to I75/64.

A modern living area is showcased, featuring a sectional sofa and two armchairs. Large windows provide expansive views of Downtown Lexington, with urban buildings visible in the background. A dining table with chairs and a small coffee table add functionality to the space.

4.81 out of 5 average rating, 113 reviews

175 LEX - Stunning Downtown Views on Main Street!

Offering unparalleled views of Downtown Lexington, immerse yourself into living like a local at 175 LEX. Condo 601 has recently been renovated featuring all the modern-day amenities a guest would desire when visiting Central KY. Residing on the 6th floor, this condo-hotel features one bedroom with a queen-sized bed, living room with sleeper sofa, full kitchen with quartz and washer/dryer in-unit. Walkable to Rupp Arena, local restaurants like Carson's, coffee shops, retail shops, & more!

A historic brick building is set amidst lush green landscaping, including neatly trimmed hedges and tall trees. The structure features a covered porch and large windows, contributing to its classic architectural style. The surrounding neighborhood is quiet, with a glimpse of the city skyline in the background.

4.83 out of 5 average rating, 24 reviews

The Equine Condo

Enjoy easy access to Rupp Arena and restaurants from this charming place to stay. Make this condo your own during your stay with all the amenities you need with a kitchen, living room, full bath, and bed. Your own private on site parking makes this location a dream stay to explore Lexington with ease. Located in the middle of downtown and walking distance to Rupp Arena or Manchester St with direct access to Keeneland and other major landmarks in Lexington you will be ready to book again!

The exterior of a spacious two-story home is shown, featuring a neutral-colored facade with large windows. A covered front porch is highlighted, framed by potted plants and shrubs, inviting guests to enjoy the fresh air. A pathway leads to the front entrance.

4.95 out of 5 average rating, 210 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 *

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.

4.91 out of 5 average rating, 221 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.

5 out of 5 average rating, 6 reviews

A spacious dining area features a long wooden table surrounded by black chairs. Exposed brick walls add character, while modern artwork and shelves are visible in the background. Soft lighting enhances the open layout that connects to a comfortable seating area.

Condo in Georgetown

The Oaks on Main.

Welcome to our spacious Airbnb located on Main Street in beautiful Georgetown, Kentucky—the heart of horse country and a prime stop along the Bourbon Trail! Nestled in a historic building brimming with character, our rental comfortably accommodates up to 8 guests. Book your stay today and get ready to create lasting memories in Georgetown, where Southern charm meets adventure! We look forward to welcoming you to our special retreat, where the best of Kentucky awaits you!

The exterior of the building is showcased at night, featuring modern lighting that illuminates the structure. A well-maintained parking lot is visible, along with landscaped areas including small trees and tidy shrubs along the sidewalk.

4.92 out of 5 average rating, 128 reviews

NEW! Private Apartment with Balcony

This apartment is the perfect location for catching a UK game, a weekend at Keeneland, business trips or clinical rotations. It 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, private balcony and convenient parking.

The kitchen features a central island with light granite countertops and a stylish gold faucet. In the background, a dining area is visible, with a long wooden table surrounded by chairs. Large windows provide natural light and a view of the spacious living area.

4.92 out of 5 average rating, 12 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.

Top guest favorite

An inviting entryway features dark gray walls and elegant white trim. A green velvet couch and a stylish table add a touch of comfort. A decorative mannequin stands nearby, reflecting light through its mirrored surface. A door leads to a bright living space, complemented by a wall-mounted TV.

4.99 out of 5 average rating, 95 reviews

Spring Specials-2 Mi. to DT- Rupp - Bourbon Trail

We Waive Airbnb Service Fees – Save 15% compared to other listings ★ 2 Mi to Rupp | 1 Mi to UK | 1 Mi to Downtown | 2 Mi to Kroger Field ★ Nestled by Woodland Park, our home offers urban convenience with serene park views. Located in the coveted Chevy Chase area, you're mins away from top restaurants, breweries, and coffee shops. Enjoy the best of Lexington from this prime location—perfect for exploring, dining, and entertainment!

A kitchenette area is displayed, featuring a dark wooden cabinet with a sink, a microwave, and a coffee maker. A large wall-mounted television is positioned above the counter. A door leads to an outdoor space, with a light-colored door visible on the left.