Pet-friendly vacation rentals in Jessamine County

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!

The Blue Heron Lakeside Chalet

Welcome to The Blue Heron Chalet, where tranquility meets breathtaking views on the shores of Herrington Lake. Our charming A-frame invites you to unwind in the serene beauty of Kentucky. Whether you're seeking a romantic retreat, a family vacation, or a gathering of friends, our lakeside chalet promises an unforgettable experience filled with relaxation, adventure, and cherished memories. Welcome to your home away from home in the heart of the Bluegrass and minutes away from the Bourbon Trail

Large, 1980's 3BR w/full basemt in Upscale area

Spacious 1980's, two story, 3 bedroom, 2.5 bath in desirable Lexington, Ky neighborhood. Two Queen beds, One twin bed, two pull out Lazyboy sofas. Two Roku TV's. WIFI Perfect for large families desiring a quiet neighborhood while still within the heart of Lexington. Private driveway & on street parking is permitted. 20 minutes to Keeneland, 10 minutes to Rupp Arena, 8 minutes to the hospitals and UK campus. 5 minutes to Chevy Chase. Walking distance to Kroger and restaurants. ID15082024-1

Lake side Bluff at Sunset Marina

Herrington Lake! Beautiful home located next to Sunset Marina and Resort at Herrington Lake. Located minutes from Kennedy Bridge on the Lancaster Kentucky side of Herrington Lake. Outstanding lake view with a parklike setting close to Marinas and Restaurants. Home is fully appointed with all you need for a comfortable retreat! Spend the day on the lake and relax on the deck and watch the boats go by. Located in a no wake zone and only minutes from local marinas and nearby towns. Well Kept!

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.

Home in Versailles on the Bourbon Trail

Guest house on beautiful 172-acre Country Estate in Versailles, KY (Woodford County). Large 4bd/3bth home located directly on Kentucky's famed Bourbon Trail and 15 minutes from the historic Keeneland Racetrack and Bluegrass (Lexington) airport. Bourbon fans will enjoy proximity to famous distilleries such as Woodford Reserve, Four Roses, Buffalo Trace, and more. Visit the locally famous Kentucky Castle and enjoy all the activities of the world renown Kentucky Horse Park and museum.

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!!

Eleanor's House

This spacious 3 bed, 2 bath home features an open concept design that seamlessly connects the living, dining, and kitchen areas. Natural light flows throughout, accentuating modern finishes and ample space for entertaining. Step outside onto the large deck—perfect for alfresco dining, relaxation, or hosting gatherings. Enjoy a blend of indoor-outdoor living in a home designed for both comfort and style. Permit #9692

The Roosting Place

Enjoy the comforts of home while visiting charming Wilmore! We are located on a quiet street within walking distance to Asbury University and Asbury Seminary. Our guest suite is located in the daylight basement of our family home and can accommodate up to 4 guests. We are a 20-minute drive from Blue Grass Airport and Keeneland. Only 15 minutes from Shaker Village of Pleasant Hill.

Prime Location 2 Kings 2 Baths Patio & Fenced Yard

A guest favorite with 200+ 5-star reviews! This stylish 2-bed, 2-bath pet-friendly Lexington home comfortably fits families and couples. Enjoy a private, fenced backyard with a gas fire pit, a fully equipped kitchen, and two king beds. Located in the charming Hartland neighborhood, it's the perfect blend of comfort and convenience for your stay.

Your Home Away from Home

3,000 sq. ft. house in an upper-middle class neighborhood, 7 miles from the U of Kentucky and downtown Lexington; 5 miles from the airport and Keeneland. There is a small park across the street and a grocery store (Kroger) about half a mile away.

Fully Renovated | Finished Basement | Luxury Beds

Enjoy a beautifully renovated 4-bed, 2.5-bath Lexington home, your peaceful, pet- and kid-friendly retreat with a large backyard, game room, and space to relax and gather.