Pet-friendly vacation 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 favorite

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

4.91 out of 5 average rating, 150 reviews

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!

Top guest favorite

The deck area is partially illuminated at night, featuring a comfortable seating arrangement with cushions. An American flag gently flutters nearby, surrounded by lush greenery. A decorative area rug adds a touch of warmth, complementing the tranquil waters visible just beyond the railing.

Home in Harrodsburg

5 out of 5 average rating, 30 reviews

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

Top guest favorite

A yellow house is featured, set against a backdrop of bare trees and blue sky. A concrete pathway leads to the entrance, which is framed by a railing. The surrounding grass provides a natural feel, while glimpses of water and boats are visible in the distance.

Home in Lancaster

5 out of 5 average rating, 31 reviews

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!

Top guest favorite

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

4.96 out of 5 average rating, 138 reviews

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.

Guest favorite

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

4.88 out of 5 average rating, 223 reviews

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!

Top guest favorite

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

4.97 out of 5 average rating, 132 reviews

Lex Family&Friends Paradise: 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, 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!

Top guest favorite

A spacious guest house is set against a clear blue sky, featuring a wraparound porch with white railings. The exterior showcases a combination of light siding and wooden accents, with dormer windows adding charm. Lush green grass surrounds the property.

Home in Versailles

5 out of 5 average rating, 46 reviews

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.

Guest favorite

Home in Lexington

4.85 out of 5 average rating, 87 reviews

Sweet 16 Stay • Minutes to Rupp

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! #leisure travelers #families with children #pet owners

Guest favorite

A cozy living area features two large sofas, complementing a rustic wooden coffee table. The space is illuminated by a floor lamp next to one sofa. Artwork, including butterfly prints and nature scenes, decorates the walls, while a patterned area rug adds texture.

Home in Versailles

4.87 out of 5 average rating, 116 reviews

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!!

Top guest favorite

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

4.85 out of 5 average rating, 41 reviews

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

Guest favorite

A cozy living area features a light gray couch and a wooden loveseat with soft cushions. A coffee table sits between them, positioned in front of an electric fireplace. A small TV is placed on a stand nearby, and large windows allow natural light into the space.

Guest suite in Wilmore

4.92 out of 5 average rating, 302 reviews

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.

Superhost

A cozy living area is presented with a plush sofa, accented by neutral tones and patterned throw pillows. A circular chandelier hangs above, while a bookshelf filled with books and decor pieces adds character. Two wooden chairs and a small table complete the inviting space.

Guesthouse in Nicholasville

4.69 out of 5 average rating, 13 reviews

Breathtaking Horse Farm views, private! Keeneland!

Welcome to the Kinlark Guesthouse, nestled in the heart of horse country on a 10 acre estate. Wake up each morning overlooking horse paddocks and rolling hills. Fully equipped & renovated home with private entrance, parking area and deck. This space is the perfect retreat for your visit to Kentucky! *Each guest on the reservation must be approved by hosts prior to booking