Vacation rentals with a pool in Lexington

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.

4.9 out of 5 average rating, 181 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

4.95 out of 5 average rating, 84 reviews

A historic log cabin is set against a backdrop of autumn foliage, showcased by bare trees with scattered leaves. The stone wall in the foreground adds a rustic touch to the landscape, leading the eye towards the inviting structure of the cabin.

Cabin in Paris

1791 Cabin on Historic Horse Farm

This rare 1791 log cabin is located on Houstondale Farm, a working horse farm in the renowned Bluegrass region of Ky. You can stroll to the barn and visit the horses or enjoy the peace and quiet before relaxing at the pool, complete with a grill and outdoor dining area. It is a scenic 22 minute drive from the Ky Horse Park, 25 minutes from Lexington, and 30 minutes from Keeneland Race Track. Even with the remote feel of the farm you will only be a mile from Walmart, shops & downtown Paris.

Superhost

A spacious outdoor area features a rectangular pool surrounded by a concrete patio. A slide is positioned at one end of the pool, while lounge chairs and a table with umbrellas provide shaded seating nearby. The two-story home, with various windows, overlooks the pool.

4.64 out of 5 average rating, 45 reviews

Private for 4 No cleaning fee Discounts up to 20%

Renovated home, quiet, established neighborhood. Perfect for solo travelers, pairs of friends or couples- no pets, children or infants. Registered guests only on this property. Walk to grocery, drugstore, coffee, fast food and dine in restaurants, banks and gas. 3.5 miles from I-64/I-75; within 5 miles of Bluegrass airport, Keeneland, KY Horse Park, Rupp Arena/downtown, distillery district, hiking and biking trails. Guest space has own entrance, and is separate and independent of host's space.

Vacation home in Nicholasville

A spacious backyard features a private swimming pool surrounded by a concrete patio. Lounge chairs and an umbrella provide shaded seating options. The two-story lodge is visible in the background, with a covered porch extending across the upper level and lush greenery surrounding the area.

5 out of 5 average rating, 19 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.

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.

4.88 out of 5 average rating, 112 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!

4.97 out of 5 average rating, 32 reviews

A view of the charming cottage is captured from the pool area, showcasing the inviting exterior surrounded by greenery. Sun loungers are arranged around the pool, providing a space for relaxation under the clear blue sky.

Guesthouse in Georgetown

Cozy Cottage on Horse Farm

Welcome to The Cottage on Karuna Farm! Located 12 min from Kentucky Horse Park in Georgetown on a cul-de-sac, we invite you to our 10 acre sporthorse farm. Efficiency cottage with one queen bed and a queen pull-out couch, full kitchen, bathroom with shower. Enjoy a relaxing time by our pool, this peaceful and private guesthouse offers a lovely respite after a long day. Sweet, friendly border collie lives on property. Easy access to Lexington, Frankfort, Midway, Keeneland…

4.91 out of 5 average rating, 261 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, 82 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**

An inviting heated pool is surrounded by manicured landscaping, featuring tall grasses and colorful plantings. A water slide adds a playful element, and shaded areas are provided by large umbrellas. The pool's clear blue water reflects the bright sunlight.

5 out of 5 average rating, 72 reviews

House w/private pool & hot tub, dogs ok

Enjoy exclusive access to incredible amenities including a heated in-ground pool, hot tub, BBQ grills, fire pit, playset, hammock, and yard games surrounded by a fenced backyard. Located on Lexington's west side, just 3 miles from Keeneland Race Course & Bluegrass Airport, and a short 4.9-miles to downtown. The pool is OPEN for the 2025 season. Dogs welcome with prior written agreement from host and an additional pet fee.

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, 102 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

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Popular amenities for Lexington rentals with a pool

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House rentals with a pool

5 out of 5 average rating, 51 reviews

A modern house is set against a vibrant blue sky, showcasing a large swimming pool with a slide. Sun loungers are positioned around the pool area. Lush greenery surrounds the home, creating a serene outdoor space for relaxation.

Home in Nicholasville

Cliff House

DavidRating, 5 stars2 weeks ago

The Cliff House is a wonderful house that has many amenities. We loved the environment, the spaciousness, the pool. The kitchen has everything we needed. We had a wonderful stay. It requires a drive to anywhere. Angela was very responsive and provided suggestions when asked. Very helpful!

A rectangular pool is set within a concrete deck, surrounded by colorful murals depicting 'Southland Swim House.' Lounge chairs are positioned along one side, with a shaded area created by an umbrella. Lush greenery is visible in the background, complementing the outdoor space.

4.81 out of 5 average rating, 75 reviews

Southland Swim House

Mary CayeRating, 5 stars7 months ago

The house was very clean. The door lock box was very easy to use. The beds were comfortable. The house was tastefully decorated. If you have seniors looking to stay, getting in and out of the shower could be difficult. The neighborhood was convenient to many stores and restaurants. The outdoor space was beautiful however we did not get to enjoy it bc our weekend was full of activities. Elizabeth the host was easy to communicate with. I would definitely stay there again.

4.99 out of 5 average rating, 88 reviews

A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.

Home in Midway

The Bees Wing

JessieRating, 5 stars1 week ago

We went for a girls weekend it was the perfect get away! The screened on in porch was our save haven for the weekend . So peaceful and loved walked to downtown areas .

5 out of 5 average rating, 15 reviews

A refreshing in-ground pool is surrounded by a wooden deck and lounge chairs, offering a perfect spot for relaxation. Lush greenery lines the property, and seating areas with umbrellas provide shaded spaces for gathering. The exterior of the home features large windows that invite natural light.

Home in Georgetown

Horse Country at The Palm House-Update Ranch home

EileenRating, 5 stars2 months ago

This house is fantastic. Comfortable beds, extremely clean, stocked kitchen utensils, and great instructions for everything in the house. This is a very nice neighborhood and we felt extremely safe. Close to restaurants and shopping. The house exceeded our expectations.

5 out of 5 average rating, 11 reviews

Home in Richmond

Heart of Richmond

VanitraRating, 5 stars6 days ago

This Airbnb was definitely more than I could have imagined. Very clean, very comfortable, very homey. Kitchen has everything you could possibly need. Safe for small children. I loved everything about this house. Sherri was wonderful as well. Very fast response time. Very respectful and reasonable. Will be booking again in the near future.

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

JoshRating, 5 stars7 months ago

Overall great stay ! Exactly as described from the hot tub down to the amenities in the house. Very peaceful area and very easy to get to many area attractions! Thank you Joe !

4.91 out of 5 average rating, 33 reviews

An aerial view captures 26 acres of open land, bordered by trees and fields. Two separate houses are visible, distinguished by their blue roofs. The property includes expansive grassy areas and an outlined perimeter, presenting a vast space for gatherings and outdoor activities.

Home in Georgetown

26 acre farm sleeps up to 30

MarinaRating, 5 stars2 weeks ago

We stayed with a group of 26 and it was very comfortable and had lots of room for us to spread out. There was ample seating which was so nice for our group to eat together and visit. The outdoor area was wonderful! It's private and peaceful, I highly recommend!

A living room is presented with warm green walls and hardwood flooring. A large window framed by dark curtains allows natural light to fill the space. Comfortable seating includes two armchairs and a sofa, arranged around a central coffee table. A dining area with a table and chairs, along with a wooden cabinet, is visible in the background.

4.73 out of 5 average rating, 187 reviews

Picadome Pool Getaway

ReidRating, 5 stars1 month ago

Super solid spot with impeccable location. Anthony was responsive when needed and the spot was all we needed for the weekend. Would stay again.

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Condo rentals with a pool

A spacious living area is highlighted by a large sectional sofa, complemented by a glass coffee table. Natural light filters through multiple windows, and decorative lighting fixtures adorn the ceiling. A cozy armchair and elegant accents add to the inviting atmosphere.

4.98 out of 5 average rating, 44 reviews

Paradiso - Divine Condo, Perfect Downtown Location

SteveRating, 5 stars7 months ago

Central location for downtown, UK, and Transy. Clean and comfortable stay in a well decorated condo. A number of restaurants nearby. Enjoyed our stay.

A well-equipped kitchen features light grey cabinetry and a spacious countertop. Modern appliances in black and stainless steel are complemented by a stylish backsplash. Illuminated by recessed lighting, the area includes a variety of kitchen utensils and decorative elements, creating a functional cooking space.

5 out of 5 average rating, 103 reviews

Luxe - Your Bourbon Trail Adventure Starts Here

JaneRating, 5 stars1 month ago

John’s condo was gorgeous… beautiful furnishings, very spacious, comfy beds and bedding, plenty of kitchen and bath supplies. Great parking (nice that there were 2 spots for our use), easy access from condo to parking garage. The location could not have been better as we were in Lexington for our son’s UK graduation at Rupp arena. The only negative was the noise from the street but it wasn’t overly bothersome. Would highly recommend!

An outdoor pool is set against a backdrop of a colorful sunset. Lounge chairs are arranged around the water. The deck features a smooth surface, and a small table is positioned nearby, creating a space for relaxation and enjoyment.

5 out of 5 average rating, 17 reviews

The Big Blue Wave - 2-Bedroom Condo by Rupp Arena

PaulRating, 5 stars1 month ago

Can’t say enough good things about the hosts and their condo. It was perfect for the week! I didn’t care for the garage, but that was on me for bringing a large vehicle. Next time I will bring one of my smaller vehicles.

A spacious living and dining area features a circular dining table with a marble top and decorative bowl of fruit. Soft seating arranged around a large wall-mounted television is visible, along with colorful artwork along the walls. Natural light enters through multiple windows.

4.98 out of 5 average rating, 93 reviews

The Retreat - Bluegrass Country Starts Here

CallieRating, 5 stars2 weeks ago

We stayed here for a weekend in Lexington for a music festival. Very walkable which was so helpful. The place was spotless and the bed was very comfortable. It is in the city so there were some siren/motorcycle noises - bring earplugs if you're a light sleeper. Would highly recommend this stay to be close to the Red Mile.

A spacious living and dining area features a large wooden table surrounded by dark chairs and a decorative chandelier overhead. Natural light floods through shuttered windows, illuminating the soft-colored seating and shelves adorned with books and decor.