Vacation rentals with a pool in Jessamine County

4.97 out of 5 average rating, 136 reviews

A circular pool is surrounded by a wooden deck with seating areas and an umbrella. A gazebo provides shade, while vibrant greenery extends in the background. Lounge chairs and a swing enhance the outdoor relaxation space.

Cottage in Salvisa

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

A spacious living area features a comfortable sectional sofa arranged around a wooden coffee table. A stone fireplace serves as a focal point, complemented by subtle decorative elements. Modern light fixtures illuminate the room, creating a welcoming environment.

4.89 out of 5 average rating, 180 reviews

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

Only minutes from Kroger field and 15 min to Keeneland. The warm and inviting floor plan offers plenty of room for entertainment. Home is equipped with new luxury Tempurpedic mattresses 4 king beds, 2 queens and 2 air mattresses. This house has a vaulted screen porch overlooking the park-like back yard which opens freely to Merrick Park . Patio is set up to BBQ and enjoy your favorite sports with an outdoor TV. Plenty of restaurants and entertainment nearby. The swimming pool is open from Apri

5 out of 5 average rating, 10 reviews

Home in Richmond

Heart of Richmond

Welcome to your home away from home in the heart of Richmond, KY. This beautiful retreat offers everything you need for a memorable and relaxing stay. Perfectly positioned to put you at the center of all things Richmond, this oasis combines convenience with comfort and style. The highlights of the property are the salt water pool and the covered back patio. Take a dip, read a book, lounge comfortably or fire up the grill, the choice is yours! Come see us and make some memories!

A large, in-ground pool reflects the surroundings, framed by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a spacious deck attached to the house. The inviting outdoor space is ideal for relaxation and enjoyment.

4.87 out of 5 average rating, 111 reviews

4 BR 3 Bath 9 beds! Hot Tub, Pool, Movie room!

Welcome to The Komi. This 4 bed, 3 bath home is an oasis in the middle of Lexington. This cozy getaway has SO much to offer; in ground pool, hot tub, stone fire pit, basketball court, and thats just the outside! Inside boasts an open floor plan living area with a HUGE dining table. Three bedrooms upstairs along with two baths. Downstairs is the perfect place for the kids with bunk bed trundles that sleeps up to 8. Oh, and did I mention the home movie theater! The Komi has it all!

4.91 out of 5 average rating, 260 reviews

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

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.

A bright and inviting outdoor area features a refreshing swimming pool with clear blue water. Surrounding the pool are sun loungers and a shaded gazebo, set against a backdrop of lush trees and well-maintained landscaping.

4.97 out of 5 average rating, 115 reviews

Summer Bliss! Pool&FunZone Oasis! 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!

4.99 out of 5 average rating, 81 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.

4.98 out of 5 average rating, 104 reviews

An in-ground pool stretches across the view, reflecting the clear blue sky. The sleek edges complement the modern design of the nearby house. Lush grass borders the pool area, enhancing the serene setting of the property surrounded by nature.

Home in Georgetown

Modern Farmhouse/20 acres/9 miles from Horse Park

Beautiful new home (built in 2018) on 20 acres just outside Lexington. 19 miles from the Blue Grass Airport & Keeneland Racetrack. 9 miles from the Horse Park. In-ground pool (open beginning of May-end of Sept, not heated). Marble wrap around porch provides stunning views of the bluegrass. *Please note that we are firm on our '4 night minimum' policy, no exceptions. **Please read about our WIRELESS INTERNET SIGNAL before booking**

Superhost

A dual-level deck houses an above-ground swimming pool with clear blue water. Two custom wooden chairs provide seating near the pool's edge, framed by a brown fence and lush greenery in the background. The deck surface is finished in light grey, enhancing the outdoor space.

Home in Lawrenceburg

4.81 out of 5 average rating, 165 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

This spacious and cozy three-bedroom home is less than one mile from Lawrenceburg's city center - nestled in a quiet, residential neighborhood with a swimming pool and dual-level deck. Downtown restaurants, grocery stores, Wild Turkey Bourbon Distillery, Four Roses Bourbon Distillery, and the city park are all within close proximity. The property was completely renovated in Spring 2019 and contains all new furniture and flooring.

A refreshing pool is surrounded by a wooden deck, featuring lounge chairs and a table with an umbrella. Floating toys are visible in the clear water, while lush greenery and trees provide a natural backdrop to the inviting outdoor space.

5 out of 5 average rating, 100 reviews

Game room! 5 beds an 4 bedrooms

POOL!! Super convenient LOCATION!! Totally renovated home with 5 beds (4 bedrooms) 2 full bath Game room! POOL opens may 26th closes sept 5 Fully stocked kitchen 1 king bed , 1queen, 3 twin beds 2 miles to Kroger field(commonwealth stadium) 4 miles Rupp arena 8 miles to keenland Less than 2 miles to Fayette mall Kroger , Trader Joe’s , many Restaurants Main Event, 1 mile away! Lex premises id 15078999

4.95 out of 5 average rating, 138 reviews

The exterior of a white one-story house features a patio area with a clear blue pool. Six metal chairs are arranged around the pool, and a small table is placed nearby. Lush green grass surrounds the pool area, and trees are visible in the background.

Farm stay in Harrodsburg

The Bunkhouse at Big Red Stables

There is no better way to experience Kentucky than horseback riding the rolling hills of the Bluegrass. Big Red Stables is happy to offer the Bunkhouse to visitors who want to ride horses, travel to nearby bourbon distilleries, go to the races or events at the Kentucky Horse Park, or just get away from it all on a third generation family farm. Horseback riding by appointment only as arranged with your hosts.