Holiday rentals with a pool in Jessamine County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jessamine County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite

Holiday home in Nicholasville

5 out of 5 average rating, 34 reviews

Stone & Cedar Lodge - pool, hot tub, fire pit, EV

Relax with the whole family at this peaceful country ranch in the heart of the Bluegrass. Sleeps 16 - 5 Bedrooms, 8 Beds, 3 Baths Located just outside of Lexington and only 12 miles from Keeneland. New 7 seat hot tub The solar heated pool is open from April until September. The tree house, swings and trampoline are big hit. Play a game of pool, basketball or corn hole. Enjoy quiet walks around the pond or roast marshmallows around a cozy campfire. Wheelchair access Level 2 EV charger.

LocationFamilyCleanliness

Home in Nicholasville

The Grand on Broadway - Pool, Hot Tub, Historic

Historic 4BR/2BA Nicholasville estate fully restored with $350K+ in upgrades, blending 19th-century elegance and modern comfort. Enjoy ornate trim, hardwood floors, soaring ceilings, 2 kitchens, grand dining, and multiple indoor and outdoor living areas. Enjoy the sounds of the birds on 1 acre with pool, hot tub, wraparound decks, porches and play field. Pet-friendly and perfect for families or groups, just minutes from Lexington, Keeneland, bourbon distilleries, and horse country.

ValueOutdoor spacesCleanliness

A private heated salt-water pool is surrounded by a spacious concrete deck, featuring two black lounge chairs for relaxation. Lush green trees provide a natural backdrop, enhancing the tranquil outdoor space. The pool's clear blue water invites enjoyment and leisure.

Guesthouse in Lexington

4.84 out of 5 average rating, 353 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

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Top Guest favourite

Home in Lexington

4.99 out of 5 average rating, 98 reviews

Close to Everything! Beautiful two-story home

Beautiful home in a great location. Less than 10 minutes to Bluegrass Airport, Keeneland, Restaurants, Downtown & Shopping. Three bedrooms and three full baths. Open concept with large, fully equiped kitchen with two dining areas and wet bar. Fireplaces in living area and master bedroom. This awesome two-story home has a fenced yard with heated pool, fire pit and outdoor area for entertaining and relaxing. Contact owner for extra charge for pool heater.

ValueLocationAir conditioning

The exterior of the home features a welcoming porch with wooden rocking chairs, surrounded by grassy areas and bare trees. The facade showcases a mix of stone and vinyl siding, and large windows provide natural light. The clear sky enhances the inviting appearance.

Home in Lancaster

4.78 out of 5 average rating, 55 reviews

The Herrington

The home is located in the quiet Herrington Lake area with a short walk to view the Lake. This beautiful home features 3300 square feet with a cozy cabin feel and all the modern amenities including two kitchens. The cabin layout provides two comfortable common areas on both floors with TVs and complimentary Wifi. The perfect place to getaway from busy demands to reconnect or find exciting adventures on the Lake.

ValueLocationBathroom

A spacious villa is showcased from the front, featuring large arched windows and a welcoming entryway. Lush greenery surrounds the property, accentuating the stone exterior. A well-maintained lawn leads up to the steps, emphasizing the tranquil setting among the trees.

Home in Nicholasville

4.91 out of 5 average rating, 11 reviews

Country Villa

Visit this country villa to get away from the city or take a vacation with the family. This home has a great outdoor entertainment area with a pool, hot tub, and outdoor kitchen/bar. The home is surrounded by rolling pastures. This home has 5 bedrooms, 9 beds, 4.5 bathrooms, a large dining room, a living room up stairs and downstairs, and a garage turned into a game area for the kids.

ValueLocationPool

Guest favourite

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, 312 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.

LocationFamilyCheck-in

Guest favourite

A spacious living area is centered around a decorative stone fireplace, complemented by a large flat-screen television mounted above. Comfortable leather seating and a wooden coffee table are arranged on a patterned area rug, with natural light entering through a nearby window.

Home in Lexington

4.88 out of 5 average rating, 49 reviews

My Old Kentucky Home

The whole group will enjoy easy access to everything from this centrally located place. ONLY 10 Minutes from LEX airport, 10 Minuets from Keeneland, 10 Minuets from Kroger Field and 12 Minutes from RUPP ARENA & Downtown LEXINGTON KY!!

LocationFamilyCondition

Top Guest favourite

A modern house is set against a scenic backdrop, featuring a landscaped yard with lush greenery. A swimming pool is positioned prominently, accompanied by lounge chairs for relaxation. A slide is also visible at the pool's edge, providing a recreational feature for guests.

Home in Nicholasville

5 out of 5 average rating, 65 reviews

Cliff House

Cliff House has to be seen to be believed. Built in 2020, it features every modern amenity in an incomparable setting along the Kentucky River palisade.

LocationFamilyLaundry

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