
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Jessamine County family-friendly rentals
Kid-friendly house rentals

Perfect for Traveling Professionals & Vacation!
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.

the Brink
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.

Cozy and Welcoming Condo
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!

Minutes to Keeneland/Airport/UK & more!
This was our second stay in Katherine’s beautiful home. Her home is clean, nice, and well appointed with everything you need for your stay. She is very responsive and helpful if you need anything at all before or during your stay. The location is great and the neighborhood is peaceful and feels very safe. I highly recommend “The Lex.” We will definitely be back for more stays when we’re in town!

Hartland: Newly Renovated 2 King Beds, Fenced Yard
We loved our stay! We were celebrating a birthday and this adorable home was perfect for our girls weekend! The hand painted artwork on the walls is beautiful and the perfect backdrop for selfies 🩷 The host was sweet enough to leave treats for the birthday girl. Great place to stay!

Fully Renovated | Finished Basement | Luxury Beds
The house was very clean, private and comfortable. The beds were super comfy and we all slept great! It was in a safe location.

Southern Hospitality! Best location close to UK!
Visiting Lexington for a work trip -- my co-worker and I thought it would be best to stay in a house rather than a hotel for a week. Cost effective, and just more comfortable. Sarah's house was perfect! Quiet, plenty of room to set up our things and work through the day, and plenty of fun places to check out in the evenings. Loved having a Trader Joe's right up the street. Absolutely LOVED the backyard -- was great to sit out there in the evenings to relax and unwind. And most importantly, it had TWO full bathrooms, which is a must for two women traveling together! Will definitely be staying here again should we find ourselves in Lexington again.

TNT’s Kentucky Estate
Kitchen had everything we needed. The work area was great.
Family-friendly apartment rentals

"Uptown Retreat" - Cozy Fireplace & Sauna
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 !!

Cute apt. 2 bedroom 3 min to Downtown & District
This is a lovely place to stay in a very peaceful and charming neighborhood! This was my second time staying here, and I’m sure it won’t be the last. It was clean, had everything I needed, and Susan was very kind and responsive. Definitely worth a stay!

Downtown Digs-Spacious Loft
We had a great stay! Easy check-in, nice and cozy place, and Molly was very responsive if we needed anything. Great location, too.

High style on the Bourbon Trail
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.

Nonie's Abode
Thanks Nora, your place was as described! Plenty of space, comfortable beds, nice area, and easy to get to Rupp Arena (5 minute drive at most). We will be back next time in Lexington

Cozy Downtown Apt - 1 block from Rupp
We had a great stay here! Lots of great coffee shops and restaurants in walking distance.

Modern Remodeled Downtown Midway Studio
Midway is so charming and my husband and I felt so lucky to be able to find Joes place for our weekend visit- it’s right in the middle of all of the cute shops, and great restaurants and bars. We were in town for a friend’s wedding but happened to arrive during the bourbon festival. It was fun to be right in the mix of the festival, and it was still quiet and peaceful at night. The place has everything we needed, comfy bed, open design, stocked kitchen, beautiful natural light, we loved the layout and just the whole feel of the place. Our host was super responsive. A/c was awesome…This place was perfect and we can’t wait to come back and stay when we visit our friends!

Haven on High Street Private Apt Historic Home
The place was great. Really interesting and nicely decorated Historic home surrounded by beautiful gardens in a great neighborhood. It was everything we hope for and more.
Family-friendly apartment rentals

Light Airy Apartment- Hiking Horses History Music
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.

Lexington's Artistic Bunker / 1BR Downtown Condo
Place was just what we needed for a couple day getaway in Lexington.

*Bluegrass Getaway*
We had a wonderful stay at Brooke’s place in Lexington! The apartment was exactly as described—clean, comfortable, and well-equipped. The area felt very safe, with secure entry into both the building and the unit itself. Brooke provided clear and helpful directions for check-in, parking, and everything we needed to know. The neighbors were also incredibly friendly, which made us feel even more at home. While we didn’t bring our dogs this time, it’s great to know that Brooke’s place is pet-friendly—we even saw a few friendly pups around the building! It’s often a challenge to find quality places that welcome pets, so we really appreciate having that option for future visits. When we return to Lexington, we’ll definitely be rebooking with Brooke!

The FLAT at Bell Place - Downtown/Horse Park
Very comfortable place. I stayed for two weeks,

*One Bedroom Apt | One Mile to Downtown Lex*
This is a beautiful, very clean and well decorated place. Quiet too. Brooke attends to the additional delails that lets you know she cares about her visitors. Popcorn left out to microwave, bottles of ginger ale in the refrigerator…. the nice touches. I liked the convenient wall unit for shampoo and body wash in the shower area. Although it isn’t appealing to walk my dogs there, there is a beautiful park down the street that we went to that worked out nicely. One thing to note…. This is a second floor apartment with lots of steps that may be difficult for seniors. Not a criticism, just an fyi. This is one of the nicest air B and B’s that I have had the pleasure of staying at.

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

Paradise Inn B&B - Lover's Suite
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.

Private Condo Downtown, Walk to Rupp Arena
Nice clean modern place in a great location. Great base for exploring Lexington with covered parking where you can leave your car as it is in such a walkable neighborhood. Close to Rupp Arena as well as the Distillery District, this beautiful modern building is great to come home to.
Destinations to explore
- House rentals Jessamine County
- Rentals with a firepit Jessamine County
- Rentals with a patio Jessamine County
- Rentals with pools Jessamine County
- Townhouse rentals Jessamine County
- Rentals with outdoor seating Jessamine County
- Pet-friendly rentals Jessamine County
- Rentals with a washing machine and dryer Jessamine County
- Rentals with a fireplace Jessamine County
- Rentals with a hot tub Jessamine County
- Rentals with lake access Jessamine County
- Flat rentals Jessamine County
- Rentals with breakfast Jessamine County
- Family-friendly rentals Kentucky
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom