Pet-friendly vacation rentals in Jessamine County

4.91 out of 5 average rating, 146 reviews

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!

4.98 out of 5 average rating, 273 reviews

A porch overlooks the serene Kentucky River, featuring a wood breakfast bar with counter stools. Rocking chairs provide a cozy seating area, framed by lush greenery and views of the river's banks. Sunlight filters through the trees, enhancing the tranquil setting.

Cottage in Wilmore

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.

5 out of 5 average rating, 28 reviews

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

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

An open-concept kitchen features a large island with seating for four, complemented by granite countertops and new stainless steel appliances. Bright pendant lights hang above, while a cozy living area with a fireplace and exposed beam ceilings creates an inviting gathering space.

4.88 out of 5 average rating, 162 reviews

Fully Renovated | Finished Basement | Luxury Beds

Newly Renovated!! Check out this Charming 4 bedroom 2.5 bath ranch style home. This home features tons of improvements including new flooring, new custom kitchen cabinets, kitchen island, back splash, granite countertops and brand new stainless steel appliances! The bathrooms feature new custom shower and new vanities. Full finished walk-out basement and fresh paint throughout! Video Surveillance: – The Property has 1exterior cameras placed as a doorbell camera. This video footage is not shar

A single-story brick house is nestled among greenery, featuring a front porch with steps leading to the entrance. Large windows are adorned with blue shutters, enhancing the inviting facade. A well-maintained lawn extends to the sidewalk, with flower beds adding a touch of color.

4.96 out of 5 average rating, 90 reviews

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

5 out of 5 average rating, 31 reviews

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

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!

Superhost

A comfortable living area features a blue velvet sofa with decorative pillows, positioned in front of a modern glass coffee table. A mounted television displays a serene landscape. A cozy fireplace is situated beneath the TV, complemented by light-colored walls and a patterned area rug.

Apartment in Lexington

4.78 out of 5 average rating, 102 reviews

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.

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.

4.89 out of 5 average rating, 207 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!

5 out of 5 average rating, 14 reviews

Aerial view of a spacious cabin set amidst dense greenery, with trees encircling the area. The cabin features a large brown roof and is situated on a grassy area surrounded by wooded hills, offering a serene, natural environment.

Apartment in Harrodsburg

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.

A welcoming living area is featured, accentuated by a cozy gray loveseat draped with a yellow throw. Two blue accent chairs are positioned around a rectangular coffee table. Natural light filters through white curtains, enhancing the space's openness.

4.97 out of 5 average rating, 78 reviews

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.

5 out of 5 average rating, 36 reviews

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

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.