Kid-friendly holiday rentals in Jessamine County

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Jessamine County kid-friendly rentals

Child-friendly house rentals

Guest favourite
Home in Lexington
4.89 out of 5 average rating, 175 reviews

Perfect for Traveling Professionals & Vacation!

JonathanRating, 5 stars2 weeks ago
We enjoyed our stay, and I would stay here again. It was clean, and the appliances were all very nice. I would point out that the driveway is very steep, and a few of the steps are steep as well. Be mindful of that if you are traveling with anyone with mobility issues. It is a good a value, and I would stay here again if ever in Lexington.
Top Guest favourite
Home in Lexington
4.97 out of 5 average rating, 115 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

GeorgeRating, 5 stars3 weeks ago
Harrison was an amazing Host! The house was immaculate and had everything you could want to feel at home and relax. This is a premier spot to take your family for Visiting the gorgeous and historic Lexington. Thank you so much for an amazing place to gather as we celebrated our son’s graduation.
Superhost
Home in Lancaster
4.92 out of 5 average rating, 78 reviews

the Brink

MichaelRating, 5 stars3 weeks ago
The view from this place is fantastic! Perched on a cliff is a great description, we were able to look down from the deck and watch birds flying up and down the Dix River basin. If you are looking for a quiet getaway or a nice place to relax after an event at Centre College, this is the place for you. The sitting area on the porch was a favorite and the weather was perfect during our stay; the pleasant hum of cicadas was a joy to this entomologist's ears. The facilities were very nice with plenty of room to sit and relax in the downstairs or mid-level lounging areas. Fletcher was quick to answer questions and the stay was loved by all; I would stay here again with no reservations.
Top Guest favourite
Home in Lexington
4.96 out of 5 average rating, 24 reviews

Cozy and Welcoming Condo

LeahRating, 5 stars2 months ago
Loralee’s place was perfect for our needs! Clean and cozy! Bed is very comfortable! Enjoyed our stay! Would definitely stay again when in the area again!
Superhost
Home in Nicholasville
5 out of 5 average rating, 12 reviews

Townhouse #5 @ The Corner House

LukeRating, 5 stars11 months ago
I was in town for a week and needed a place coming solo. Karen was very responsive and helpful and recommended anything I asked about. Went out of her way to make me feel comfortable in her place! The place was clean and exactly as described!
Top Guest favourite
Home in Lexington
4.96 out of 5 average rating, 78 reviews

Minutes to Keeneland/Airport/UK & more!

MarianneRating, 5 stars1 month ago
I cannot think of one complaint - Katherine’s home was easy to find and access, spotless and as advertised. The beds were very comfortable, the neighborhood was quiet and we thoroughly enjoyed our stay!
Guest favourite
Home in Lexington
4.89 out of 5 average rating, 152 reviews

Fully Renovated | Finished Basement | Luxury Beds

KrisRating, 5 stars3 weeks ago
The house was very clean, private and comfortable. The beds were super comfy and we all slept great! It was in a safe location.
Superhost
Home in Lexington
4.87 out of 5 average rating, 23 reviews

TNT’s Kentucky Estate

ThomasRating, 5 stars1 week ago
Kitchen had everything we needed. The work area was great.

Kid-Friendly apartment rentals

Top Guest favourite
Apartment in Lexington
4.95 out of 5 average rating, 205 reviews

Canopy of trees

SarahRating, 5 stars1 week ago
A beautiful downstairs unit. it's across the street from Henry Clay Park, which was lovely for evening walks. I was able to walk easily to UK Music building in about 25 minutes, and there are restaurants and a Kroger's midway.
Top Guest favourite
Apartment in Lexington
4.98 out of 5 average rating, 203 reviews

"Uptown Retreat" - Cozy Fireplace & Sauna

HeatherRating, 5 stars2 weeks ago
we almost were not about to return and book with Air B n B but...David absolutely changed that and turned our past awful experience right side up!!! During a extremely busy weekend and sold out everywhere weekend , he was available and even let us check in early!!! we couldn't get over just how peaceful stress-free and felt like honestly we were at our home! they didn't hover or intrude . Will return !!
Superhost
Apartment in Lexington
4.89 out of 5 average rating, 114 reviews

Downtown Digs-Spacious Loft

TannerRating, 5 stars6 days ago
Super easy stay! close to a bunch of spots. super chill little loft. thanks!
Top Guest favourite
Apartment in Versailles
4.98 out of 5 average rating, 336 reviews

High style on the Bourbon Trail

NicholeRating, 5 stars6 days ago
One of the nicest Air bnbs I’ve ever stayed in! The apartment was spotless and beautifully decorated—every detail felt thoughtfully curated. I really appreciated the extra blankets, pillows, and towels provided, which made the stay even more comfortable. The location is absolutely perfect for anyone exploring the Bourbon Trail—just a short drive to Wild Turkey, Four Roses, and Buffalo Trace. Plus, there’s a charming coffee shop, a fun bourbon bar, and a pool hall with surprisingly great food all within walking distance. Truly a gem of a place—I’ll definitely be back.
Guest favourite
Apartment in Winchester
4.89 out of 5 average rating, 151 reviews

The River House Floor 2 Getaway, w/a river view.

ManuelRating, 5 stars6 days ago
very clean and beautiful place, inside and outside. would go again for sure👍🏽
Top Guest favourite
Apartment in Lexington
4.94 out of 5 average rating, 137 reviews

Nonie's Abode

JeanneRating, 5 stars2 weeks ago
we had a relaxing and peaceful stay at Nora's place. The beds were very comfortable, great shower and spacious living space. also a beautiful deck and gardens outside! thank you!
Guest favourite
Apartment in Lexington
4.9 out of 5 average rating, 297 reviews

The Flat @ West Second

DierdraRating, 5 stars2 months ago
Super comfortable private apartment with free and safe street parking just blocks from historic Lexington downtown. Hosts were responsive and welcoming. Would definitely go back! Thank you so much, Breck and Linda!
Top Guest favourite
Apartment in Lexington
4.96 out of 5 average rating, 200 reviews

Cozy Downtown Apt - 1 block from Rupp

KariRating, 5 stars1 week ago
Booked the stay for an event at rupp arena. Easy walking distance to arena and many restaurants. Host was quick to respond and very helpful. Cute and clean!

Child-Friendly Holiday Condos

Top Guest favourite
Condo in Frankfort
4.93 out of 5 average rating, 118 reviews

Light Airy Apartment- Hiking Horses History Music

LandonRating, 5 stars1 week ago
The place was very clean, tidy, and we'll stocked. Within walking distance to the capital and a few restaurants. A very short drive to more restaurants and stores. Amelia was thoughtful, responsive, and proactive without being overbearing at all. I recommend her place for sure.
Guest favourite
Condo in Lexington
4.91 out of 5 average rating, 225 reviews

Lexington's Artistic Bunker / 1BR Downtown Condo

GuyRating, 5 stars4 weeks ago
Thank you for great accommodation. Will be happy to stay again!
Top Guest favourite
Condo in Lexington
4.95 out of 5 average rating, 214 reviews

The FLAT at Bell Place - Downtown/Horse Park

CassidyRating, 5 stars3 weeks ago
I cannot say enough great things about Matt and the house! We traveled for a girls trip, Matt’s house was clean and safe. He responded to every question, politely and quickly! Recommend great restaurants, delicious food! I will definitely be booking with Matt again in the future!
Guest favourite
Condo in Lexington
4.93 out of 5 average rating, 164 reviews

Across From UK Hospital-Weekly/Monthly Discounts!

JalessaRating, 5 stars3 weeks ago
This place was beautiful, spacious & close every place i needed to go. Brandon was very responsive & helpful. The bed was super comfortable, definitely will book again in the future.
Guest favourite
Condo in Lexington
4.91 out of 5 average rating, 128 reviews

💙The FLAT @ the LEX w/ Parking-Horse Park-Bourbon

EmilyRating, 5 stars4 weeks ago
This was a great place to stay, super clean and less than a mile from Rupp. We didn't get to make use of the host's suggestions for things to do this trip, but I'll already be looking forward to a second trip!
Guest favourite
Condo in Paris
4.94 out of 5 average rating, 114 reviews

Paradise Inn B&B - Lover's Suite

MelissaRating, 5 stars2 weeks ago
we loved our stay at the paradise inn! we will absolutely be back to Paris, KY. Ajs paradise Cafe right below is was such a nice treat and delicious food! Lee was by far the best, would recommend this stay to everyone.
Superhost
Condo in Lexington
4.87 out of 5 average rating, 134 reviews

Private Condo Downtown, Walk to Rupp Arena

JackRating, 5 stars3 weeks ago
This place is perfect for a stay in downtown Lexington! Keene was a great host and the space itself was well kept and beautiful.
Top Guest favourite
Condo in Frankfort
4.97 out of 5 average rating, 153 reviews

Bourbon Trail R&R

HeatherRating, 5 stars3 weeks ago
Perfect place for us. Comfortable. centralized location while still being set back from the main road.

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