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

Pool | Hot Tub | Covered Porch | Patio | Game Room

Only minutes from Kroger field and 15 min to Keeneland. The warm and inviting floor plan offers plenty of room for entertainment. Home is equipped with new luxury Tempurpedic mattresses 4 king beds, 2 queens and 2 air mattresses. This house has a vaulted screen porch overlooking the park-like back yard which opens freely to Merrick Park . Patio is set up to BBQ and enjoy your favorite sports with an outdoor TV. Plenty of restaurants and entertainment nearby. The swimming pool is open from Apri

Hot tub, lake view, tremendous deck/outdoor space

Welcome to the most private lake home for rent on Herrington. Direct lake access and centrally located to 4 marinas with-in 1.5 miles. This peaceful home is on a 1.7 acre double lot with over 300’ of frontage and backyard with dozens of mature trees. The private cove is perfect for swimming, kayaking, and hanging out on the water throughout the day. The 2,500’ SF 4 bedroom home was remodeled in 2024 with large groups in mind. If you’re looking for a one of a kind private setting, this is it!

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!

Blue and gray modern apartment!

This place is in a townhouse that has been divided it,your Airbnb is above,your don’t share with anything is designed for the best short-term rental experience.Easy access to the following: - Less than 6 miles Rupp Arena, Kroger Field, Downtown, and UK Campus - 10.5 miles from LEX airport & Keeneland - 4.0 miles from Hamburg Pavilion - 5 minutes to main grocery stores - 5 miles to I-75 2 min access to new circle rd. Driveway parking is available Perfect place to stop to rest from a long road.

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.

Perfect for Traveling Professionals & Vacation!

Traveling professionals, relocation guests, vacation guests, this is the perfect house for you! This 3 bedroom 2 bath ranch-style home w/ a garage has a gourmet kitchen and an open floor plan. Perfectly located in the heart of Lexington in a family-friendly neighborhood near Trader Joes, hospitals, restaurants, the Summit Shopping Center, Fayette Mall and a short trip to Keeneland or downtown Lexington. This is the perfect home away from home. All are welcome! Pet Friendly, per request!

Cozy, quiet, comfortable apartment. In the woods.

Take a break and unwind in this quiet basement apartment in a cabin in the woods. Gated community with no through traffic. Nestled on over five acres of woods. Lots of easy groomed trails with fire pits. 3 miles from historic Shakers Village. 12 miles from Fort Harrod. 8 miles from Harrington lake. 20 miles from Perrysville Historic Battlefield. Conveniently located on the Bourbon trail. only 23 miles from Lexington Bluegrass airport. 22 miles from Keenland horse track and Red mile gaming.

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!!