Kid-friendly holiday rentals in Jessamine County

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Jessamine County

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

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Guest favourite

Flat in Wilmore

4.98 out of 5 average rating, 244 reviews

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

29 Oct – 5 Nov

$69 SGD per night

Guest favourite

Cottage in Wilmore

4.98 out of 5 average rating, 166 reviews

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

18–25 Oct

$171 SGD per night

Guest favourite

Guest house in Nicholasville

4.98 out of 5 average rating, 298 reviews

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.

23–30 Jun

$128 SGD per night

Guest favourite

Farm stay in Nicholasville

4.93 out of 5 average rating, 241 reviews

Moonlit Meadows: A Kentucky Getaway for Travelers

Escape to the heart of Kentucky's countryside in our modern guest suite, set across a 17-acre landscape. Immerse yourself in the serenity of nature with views of a pond and beautiful rolling fields. Ideal for both business and leisure travelers as well as those visiting Asbury University. Our guest suite has continued to offer a tranquil haven where you can relax and rejuvenate! Enhance your experience by visiting the great grandson of the legendary Secretariat, stabled just 4 miles away.

14–21 Oct

$140 SGD per night

Guest favourite

Farm stay in Lancaster

5.0 out of 5 average rating, 145 reviews

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

13–20 Feb

$279 SGD per night

Guest favourite

Flat in Wilmore

4.93 out of 5 average rating, 251 reviews

Travelers Loft - Asbury & Lexington area apartment

You deserve a unique and simple guest experience! This full apartment with an upstairs sleeping loft is located in Wilmore for you. ► A short walk from Asbury University and Seminary ► 25 minutes from Lexington, Keeneland, UK, and the airport ► A quiet neighborhood with green space ► Upstairs loft bedroom with low, pitched ceilings ► Secure keyless entry ► Hi Speed Internet ► Roku TV ► Peaceful & secure ► Keurig coffee maker ► One set of towels and sheets for stays less than a week

25 Sep – 2 Oct

$120 SGD per night

Guest favourite

Flat in Lexington

4.99 out of 5 average rating, 203 reviews

Lexington Apt. with parking & private entrance

Lower level apartment with parking and two entrances. Light painted walls, ceiling lighting/fan, plus free washer and dryer. Approximately 10-15 minutes from Bluegrass Airport, 15-20 minutes to the University of Kentucky campus, stadium and 20-25 to Rupp Arena, 10-15 minutes from main entrance to Keeneland Race Track Main entrance, 20-25 minutes to downtown Lexington, 10-15 minutes to shopping mall/restaurants located in mall area, 50 minutes from the ARK ENCOUNTER AND CREATION MUSEUM.

26 Nov – 3 Dec

$102 SGD per night

Superhost

Home in Lexington

4.82 out of 5 average rating, 483 reviews

Modern and Spacious Home w/ 5.1 Theater

(Also click my host picture to see our newest Airbnb "Elegant & Inviting Home with 5.1 Theater") Open space, natural light, and charming décor greet you at our well-adorned duplex in the established Merrick area in Lexington! Walk to Malone’s, Baskin Robbins, Fresh Market, and many other nearby shops. Bask in modern furnishings, memory foam beds, equipped kitchen, full-size laundry room, and high speed Wi-Fi. Movie nights are a blast with the huge 84” projector screen and surround sound!

17–24 Jun

$133 SGD per night

Guest favourite

Home in Lexington

4.91 out of 5 average rating, 566 reviews

Lower Level of Home near UK, Eateries, 1000 sq ft

Large private sunny apt w/ lovely deck in a safe, quiet neighborhood 5 mins from LEX airport. 15 minutes from UK. Walking trail in neighborhood. 2Q beds in separate rooms, full private bath, pool table, microwave, coffee maker, frig, large flat screen TV with Roku, Netflix. Deck with view of beautiful yard with mature trees, swing, chiminea, bridge and path through garden. Welcome from Chris! NOTE! As ALWAYS, ALL bed linens & bath towels washed, bleached & sanitized after every guest!

7–14 Dec

$97 SGD per night

Guest favourite

Cabin in Nicholasville

4.95 out of 5 average rating, 244 reviews

National Historic O'neal Cabin

Built during the late 1700’s, the two-story log cabin was reconstructed in 1995 and updated in 2019. The O'neal Cabin is listed on the National Register of Historic Places. Located in central Kentucky, six miles from historic downtown Lexington, the O’Neal Log Cabin is in the heart of horse country and the bourbon trail. Whether you are looking for a getaway, a place to stay during the horse sales or a retreat while you visit Lexington’s sites, the O'Neal Log Cabin is perfect retreat.

6–13 Jan

$228 SGD per night

Guest favourite

Home in Nicholasville

4.92 out of 5 average rating, 213 reviews

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. It looks brand new on the inside and has an awesome 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.

27 Dec – 3 Jan

$185 SGD per night

Guest favourite

Guest house in Wilmore

4.95 out of 5 average rating, 133 reviews

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.

21–28 Dec

$132 SGD per night