Pet-friendly holiday rentals in Jessamine County

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Top-rated pet-friendly home rentals in Jessamine County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite

An airy living space is showcased, featuring large windows that invite natural light and provide views of the surrounding fields. Comfortable seating arrangements with a mix of couches and chairs are positioned around a central area rug, highlighting a handcrafted coffee table and a wood stove.

Chalet in Wilmore

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!

4.92 out of 5 average rating, 157 reviews

Superhost

Cabin in Lexington

Rural Kentucky River Palisades Cabin/Past Distilry

Fabulous Cabin & Views of Kentucky River Palisades;Rural Escape 20 minutes S of Lexington;Scenic & Treasured Landscape.View wildlife,Rock Formations,Fall Colors.One mile riverfront,boat ramp&fishing lake;Kayaks&Pontoon Boat avail(xtra fee)Hike & explore 57 acres. History abounds:Site of 1860 Bourbon Distillery;Daniel Boone lived & surveyed from Boone’s Knoll;Loretta Lynn&Dolly Parton performed here;Camp Nelson Civil War National Landmark adjacent;Paul Sawyier’s chosen spot for plein air painting

4.83 out of 5 average rating, 258 reviews

Top guest favourite

Home in Lexington

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

4.95 out of 5 average rating, 110 reviews

Top guest favourite

Home in Lexington

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

Picture this: sunlight glints off the pool, the hot tub steams as evening settles over Lexington's Lanesdown Park, and fourteen of your favorite people crowd the dining table for one more story before bed. This is your Bluegrass basecamp — five bedrooms, three and a half baths, a basement game room, and a backyard built for slow mornings and long nights. The trip you'll talk about for years starts right here. WHO THIS HOME IS BEST FOR Multi-generational families in town for a Keeneland race da

4.91 out of 5 average rating, 211 reviews

Top guest favourite

An outdoor area is visible, featuring a fire pit surrounded by several chairs and a picnic table. Lush green grass is present, complemented by trees in the background. An active railroad bridge looms above, with soft, diffuse light filtering through the clouds.

Cabin in Wilmore

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.

4.96 out of 5 average rating, 202 reviews

Guest favourite

A spacious living area features a comfortable grey sofa and armchairs arranged around a white coffee table. Light-colored curtains frame large windows, while a dining area with a dark wood table is visible in the background, alongside a modern kitchen with stainless steel appliances.

Home in Lexington

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!

4.89 out of 5 average rating, 254 reviews

Top guest favourite

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

Home in Lexington

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

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, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

4.97 out of 5 average rating, 152 reviews

Top guest favourite

Home in Versailles

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.

5.0 out of 5 average rating, 65 reviews

Guest favourite

Home in Versailles

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!!

4.84 out of 5 average rating, 147 reviews

Top guest favourite

Home in Lexington

Room of Requirement Guest Suite STR #15063219-1

This space, my fully furnished, walk-out basement, is available again! Nestled in the middle of a centrally located neighborhood, I offer a comfortable space with private parking and access, while still only 10 minutes to University of Kentucky, 15 minutes to Bluegrass Airport & Keeneland and 25 minutes to the Kentucky Horse Park. Five restaurants, ice cream, coffee shop, grocery market, boutique shops are a 5 min walk away.

4.92 out of 5 average rating, 134 reviews

Superhost

Home in Nicholasville

The Lodge A-Frame Getaway

Tucked away in a wooded retreat along the Kentucky River in Nicholasville, this secluded and peaceful getaway is full of character. Sleeping 8 with 4 bedrooms and 3 baths, it features a large, fully equipped kitchen and a fun game room. Enjoy nature and privacy while staying just minutes from Lexington, Keeneland, the Bourbon Trail, wineries, hiking, and local dining—an easy drive to Central Kentucky’s top attractions.

4.94 out of 5 average rating, 16 reviews

Guest favourite

The exterior of a one-story home is shown, featuring a welcoming front porch with steps and wooden railings. A well-maintained lawn surrounds the property, complemented by neatly arranged shrubs. Clear skies enhance the visibility of the home's facade.

Home in Wilmore

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

4.86 out of 5 average rating, 58 reviews