Family-friendly vacation rentals in Jessamine County

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Top-rated family-friendly rentals in Jessamine County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An airy living space is showcased, featuring large windows that invite natural light and provide views of the surrounding fields. Comfortable seating arrangements with a mix of couches and chairs are positioned around a central area rug, highlighting a handcrafted coffee table and a wood stove.

Chalet in Wilmore

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

KitchenIndoor spacesPets

4.92 out of 5 average rating, 157 reviews

Top guest favorite

A cozy bedroom features a full-sized bed draped in a patterned blue and white coverlet. A bedside lamp and a small table with decorative items complement the space. Natural light filters through a small window, creating a serene ambiance.

Apartment in Wilmore

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

KitchenIndoor spacesLocation

4.97 out of 5 average rating, 386 reviews

Top guest favorite

A bright and airy interior is displayed, featuring wooden double doors that open to an inviting space. A dining table is set with rustic design, while a cozy sleeping area is positioned in the background. Natural light enhances the warm tones of the decor.

Tiny home in Lexington

Horse & Barrel Haven

This precious tiny house in the horse and bourbon capital of the world is anything but ordinary and lets talk about Location, Location, Location! Located only 3.1 miles from the Lexington Bluegrass Airport and 3.9 miles from Keeneland Racetrack. Only 4.6 miles from the University of Kentucky and only 5.3 miles from downtown Lexington. Only 3.5-5 miles from several hospitals. Great restaurants and shopping are an easy 3-7 minute drive! Great work or leisure space w/several cozy sleeping options.

KitchenIndoor spacesLayout

5.0 out of 5 average rating, 106 reviews

Top guest favorite

Lush green grass frames the scene, with two flowering trees prominently in the foreground. A wooden fence lines the area, leading to a cottage that is partially obscured by the trees. Natural light brightens the surroundings on a clear day.

Guesthouse in Nicholasville

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.

KitchenIndoor spacesHospitality

4.98 out of 5 average rating, 397 reviews

Top guest favorite

An outdoor area is visible, featuring a fire pit surrounded by several chairs and a picnic table. Lush green grass is present, complemented by trees in the background. An active railroad bridge looms above, with soft, diffuse light filtering through the clouds.

Cabin in Wilmore

Highbridge River Cabin, Private Dock, EV Charger

Relax at the river cabin. Retreat right on the Kentucky River with private dock for easy river access. The cabin has Dual Plug Type 2 EV charger. Cozy cabin on stilts with stone fireplace & porch with table and chairs. Surrounded by nature & beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 mins or less from LEX Airport, Keeneland and Shaker Village. No extra guests without permission, no parties.

Indoor spacesFamilyComfort

4.96 out of 5 average rating, 202 reviews

Top guest favorite

A spacious lounge area is visible, featuring a leather sofa and a vintage chest serving as a coffee table. The open kitchen is equipped with modern appliances, while warm lighting from a nearby lamp adds a cozy ambiance to the space. Light-colored walls complement the wood flooring.

Guest suite in Wilmore

Kinlaw Valley-View Hideaway

Your "hideaway" is conveniently situated in the Bluegrass and Bourbon Trail region of beautiful central Kentucky, just a few miles south-west of the eclectic city of Lexington. You are a short walk from Asbury University/Seminary and from the Centennial Park. Keeneland Race Track, The Kentucky Horse Park, UK, and Bluegrass Airport are within a short half hour's distance. The Daniel Boon National Forest, the Ark Encounter and Churchill Downs are each within a 90-minute picturesque drive.

FamilyIndoor spacesCleanliness

4.98 out of 5 average rating, 100 reviews

Top guest favorite

A spacious living area features a comfortable sofa adorned with patterned pillows. Natural light illuminates the wooden ceiling and warm tones of the furnishings. A decorative area rug complements a coffee table, while soft lighting from side tables enhances the inviting atmosphere.

Townhouse in Lexington

Modern Townhome Close to UK

Welcome to this modern townhome, located in the desirable Chinoe neighborhood. Steps away from Chinoe Shopping Center, you'll find a supermarket, salon, and several restaurants. It's just a quick drive to Kroger Field, and a short drive to the heart of downtown. So whether you're here to place a bet at the Keeneland racetrack, attend a concert at Rupp Arena, tour one of our many bourbon distilleries, or cheer on the Wildcats, you'll find that this townhome is in a convenient location.

FamilyKitchenDecor

4.97 out of 5 average rating, 119 reviews

Top guest favorite

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.

Home in Lexington

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

FamilyIndoor spacesCheckout

4.97 out of 5 average rating, 151 reviews

Guest favorite

Home in Versailles

Woodford Stables / Walk to Eckert's Orchard

Welcome to Woodford Stables, your serene retreat nestled amidst rolling hills and picturesque paddocks. This charming farmhouse boasts a modern kitchen, three inviting bedrooms, and two pristine bathrooms. Relax in the cozy living area, or step outside to savor breathtaking views. With horses grazing nearby, it's a tranquil escape. Conveniently located, you can stroll to Eckerts Orchard for a delightful local experience. Ask us about boarding your horses during your stay!!

KitchenIndoor spacesView

4.84 out of 5 average rating, 147 reviews

Top guest favorite

A spacious bedroom is featured with a large, dark bed framed by two bedside lamps. A soft, blue throw blanket adorns the bed. A painting is displayed on the wall above, and a potted plant adds a touch of greenery in the corner.

Home in Wilmore

*KY Charm*Asbury-Lex-Keeneland-King bed-spacious

This spacious, private basement is the perfect lodging for visiting families, commuting students, or out-of-town explorers. Located in a peaceful subdivision in the quaint town of Wilmore, we're within walking distance to Asbury University and Seminary, Centennial Park, hiking trails, and a bustling main street with shops, cafes, and restaurants. We are an easy 20-30 minute drive from Lexington, Keeneland, Rupp Arena, and the Bluegrass Airport. Jess Co Permit #9248

Indoor spacesFamilyHospitality

5.0 out of 5 average rating, 108 reviews

Guest favorite

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

Nicholasville's finest short term rental! We recently finished remodeling this spacious ranch home in Nicholasville Ky and are extremely excited to share it with future guests. High quality touches on the inside and has a tranqiul oasis in the backyard with water effects/ koi pond. It is close to all the great things to do in Lexington including Keeneland and the University of Kentucky. Mattresses are top of the line and will ensure you have a very comfortable stay.

Indoor spacesKitchenHospitality

4.93 out of 5 average rating, 315 reviews

Top guest favorite

A queen size bed with a carved wooden frame is centrally positioned in the bedroom, flanked by soft pink drapes. Two framed horse prints adorn the walls, complementing the elegant decor. Natural light filters softly through the windows, enhancing the room's serene ambiance.

Guesthouse in Wilmore

Coach House at the 1898 Red Bud B & B

Lovingly renovated coach house unit was originally the workshop attached to the back of the coach house. It is a ground floor accommodation with private entrance located behind the main bed & breakfast. We are only two city blocks from Asbury! We make a perfect base to explore the area. The Bourbon Trial, numerous horse farm tours, vineyards, Keeneland, the Horse Park, and historic sites such as Shaker Village of Pleasant Hill. Only 11 miles from Lexington.

Indoor spacesFamilyValue

4.96 out of 5 average rating, 169 reviews