Condo vacation rentals in Lexington

4.9 out of 5 average rating, 101 reviews

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

Offering unparalleled 270-degree views of Downtown Lexington on Main Street with a private balcony! The Penthouse is newly constructed featuring a full kitchen with quartz countertops & breakfast bar, kitchen table, balcony, 3 bedrooms each with queen-sized beds, two bathrooms, full living room with two sleeper sofas and private washer/dryer. Located in the heart of Lexington, walkable to Rupp Arena, Keeneland and Carson's, there isn't a more convenient spot to stay close to the action!

4.95 out of 5 average rating, 221 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 *

4.91 out of 5 average rating, 233 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, 13 reviews

Condo in Georgetown

The Oaks

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!

4.94 out of 5 average rating, 198 reviews

*New Cozy Apartment| 2 miles to downtown Lex*

This Beautiful Brand New Apartment is centrally located to all the Bluegrass has to offer. Great 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 looks onto the living room, simply pull the barn doors shut for privacy. Walking distance to shopping, restaurants, convenient stores, etc. 1.8 miles to Red Mile Casino, 2.5 miles to Rupp Arena, 5 miles to Kenneland!

Superhost

4.94 out of 5 average rating, 16 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.

4.95 out of 5 average rating, 155 reviews

Condo in Frankfort

Bourbon Trail R&R

Our condo is conveniently located in walking distance of the capital. Peaceful neighborhood with wide streets. PLEASE NOTE: The condo is located up two flights of stairs. Kitchen is completely equipped with everything you’ll need to enjoy your stay, including a K-cup coffee machine. (Just bring your K-cups) Frankfort is a vibrant town located in the heart of the Bourbon Trail. 1 small dog may be permitted with pre-approval - $75/stay

4.94 out of 5 average rating, 66 reviews

Gardenside Apartment: Private and Spacious

7 minute drive to Railbird! Only 2 miles to commonwealth Stadium and 3 miles to Keeneland. You will enjoy easy access to everything from this centrally located place. This 1,200 square foot apartment has everything you need for a long term or quick getaway. It is the basement unit of our personal home where we live on the first floor. There is a private entrance and parking. Large rooms - kitchen, living room, full bath and bedroom are all yours!

4.99 out of 5 average rating, 113 reviews

2Mi. To - Downtown -UK Campus-Kroger Field

💸 Save 15% – We Waive Airbnb Service Fees! ★ 2 mi to Rupp Arena • 2 mi to Kroger Field ★ 1 mi to University of Kentucky • 1 mi to Downtown Lexington Nestled near Woodland Park in the coveted Chevy Chase neighborhood, our home blends urban convenience with serene park views. Stroll to top restaurants, local breweries, and coffee shops—all just minutes away. Enjoy the best of Lexington—perfect for exploring, dining, and entertainment!

4.93 out of 5 average rating, 126 reviews

Condo in Frankfort

Light Airy Apartment- Hiking Horses History Music

Return from touring hiking, history museums, Horse park, or the Bourbon Trail to relax and dine in this super comfortable, light- filled apartment in a quiet historic neighborhood. Walk 5 minutes south to Capital gardens, governor's mansion and New Parisian style bakery. Walk 8 minutes north to the river and downtown-library, Riverwalk, canoing, in season farmers' market and concerts, coffee shop, galleries, restaurants and museums.

4.94 out of 5 average rating, 119 reviews

Condo in Paris

Paradise Inn B&B - Lover's 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.