Family-friendly vacation rentals in Fayette County

Spring Street Loft by Rupp-Covered Parking + Deck

Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!

Treetops Solar Sanctuary

Treetops is a spacious studio apartment within tree-lined walking distance of the UK campus, football stadium, medical center, Arboretum, and the Chevy Chase business area. Nearby is downtown Lexington, with its many restaurants and bars. The apartment has a kitchenette (no stove), with a microwave, toaster oven and mini-fridge. For larger parties, rent the full building! An outside stairway connects the two similar spaces, the upper of which is named "Treetops Solar Sanctuary." STR #15085005

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

*Chevy Chase TH (1) mile to UK | EV Charging*

The Moody Chevy Chaser is located in the heart of 40502! Enjoy our 2-bedroom, 1-bathroom apartment that has been recently renovated. This gem is located in the heart of the highly desired Chevy Chase where guests are able to walk to UK, the Arboretum, Kroger Field, & so much more. This unit is the right-side of a duplex equipped with all the modern-day amenities a guest could desire. Guests will live like a true Lexingtonian and will be conveniently located for all their stay needs.

BoHo Paradise - Fire Pit- Downtown - Rupp Arena

Start your mornings with fresh coffee and unwind in the indoor hammock with a good book. This cozy, boho-inspired cottage comes fully furnished in the heart of Lexington’s vibrant Distillery District. Just 1.5 miles from Rupp Arena and 5 miles from Keeneland, it’s ideally located for city excitement and classic Kentucky charm. Relax by the backyard fire pit or step out to nearby cafés, restaurants, and downtown energy. A stylish, comfortable retreat for your Lexington stay.

The Kenwick - Comfy, Clean, Chic

Lovely downtown Kenwick neighborhood w/ off street parking. Beautifully appointed space w/ amazing queen beds. Updated w/ fast wifi connection. Walking distance to a community coffee house & wine bar, a craft brewery, restaurants, bakeries and a small grocery store. * Rupp Arena 2.5 miles * Keeneland Racetrack 7.5 miles * Kentucky Horse Park 10 miles * STR Reg #15071157-7 - Maximum occupants 4 - Guests are prohibited from allowing more than maximum occupancy *

Spacious King Suite | Horses, Fire Pit, Garage

The whole family will enjoy staying in a quiet & safe neighborhood that’s close to everything! There's lots of room for fun and you'll love the large, private patio and fenced-in backyard featuring a fire pit and hammock hung under the trees. You'll have easy access to favorite local restaurants, shopping, attractions, Kentucky Horse Park, Keeneland, Rupp Arena, downtown events, & the interstate (I-75 or I-64) within minutes. Registration No. 15078410 “dash” 1

Horse Farm Cottage near Keeneland and Horse Park

Horse lovers dream and only 5 minutes from the Horse Park! This updated and professionally decorated cottage is located on a beautiful 120 acre horse farm 5 minutes from the Horse Park, 10 minutes from Keeneland and the airport, and 20 minutes from downtown Lexington. There are many activities located close by such as: horse races, horse competitions, Woodford Reserve, Buffalo Trace, and so much more!

Beautiful 4-bedroom home, close to Downtown/UK

Spacious and full of natural light, this 4-bedroom, 2-bath home is nestled in Lexington’s beloved Southland neighborhood. Walk to Southland Drive for local shops, cafes, and a local farmers market, or take a short drive to downtown, Keeneland, UK, and major hospitals. With a fully equipped kitchen, cozy living spaces, and a private backyard, it’s perfect for families, groups, or business travelers.

Short walk/ride anywhere on campus- Wkly Discount!

Welcome to Lexington! Stay in our cozy condo in the heart of the University of Kentucky campus. It's walkable or a short ride to restaurants, bars, downtown, and shopping. Take in a University of Kentucky sporting event, check out the cool nightlife, or try your luck at nearby Red Mile Racetrack or at the Legendary Keeneland Race Course! Your adventure awaits!

*Contemporary 1 BR Apt close to Downtown*

Second Floor apartment with off street parking & private secured entrance. New Apartments featuring modern appliances & furnishings. Walking distance to tap rooms, coffee shops, restaurants & bakeries. Located close to downtown Lexington - easy access to Rupp Arena, the Legacy Trail, and just a short Uber ride to the Kentucky Horse Park & Keeneland.