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!

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.

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

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!

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.

Spacious Apartment With Hidden Room

Welcome to your newly renovated cozy modern farmhouse apartment. It is large, bright, airy and welcoming. There is a large bedroom with an queen bed and an oversized closet. The kitchen is clean and simple with granite countertops. The living room is open and spacious. The bathroom sports a soothing jacuzzi tub soak while the jets relax muscles relax in the multiple jets. There is a dedicated washer and dryer. This apartment is attached to the house but there is no shared indoor space.

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!

Clean 3-BR House. Free Parking. Wi-Fi. Smart TV.

3 BR, 1.5 bath, 1-story House on cul de-sac. Wi-fi, Smart TV (No cable). Kitchen Table w/6 chairs. Sleeps 6 (2 King & 2 Twin). Love seat added for extra seating. New washer & dryer (2024). Dog friendly - no fence. Backs to Man O War Blvd., small deck. Trees for privacy. 1.7 miles to The Summit (Restaurants/shopping), 5.5 miles to UK, 8.1 miles to BG Airport, 11 miles to Keeneland. If you plan to plug in an electric car, it will be $6/day. Please let us know if cover needs to be unlocked.

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!!

Lexington Holiday FUN-ZONE! Pool! Hottub! GameRm!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, a sporting event, or just looking for a fun getaway, we have all the entertainment you need! Featuring a pool, hot tub, arcade machine, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!

Guest Favorite/2 Kings/Fenced Yard/Prime Location

Guest Favorite Stay in Lexington’s desirable Hartland area! Relax in 2 comfy king bedrooms, enjoy a fenced yard perfect for pets, and unwind on the patio with fire pit & string lights. Fully renovated with a stocked kitchen, smart TVs, and in-home laundry. Walk to parks, jog-friendly sidewalks, and local dining. Minutes to downtown, UK, and distilleries. Perfect for families, friends, or pups—your Lexington getaway starts here!