
Holiday rentals with a pool in Kentucky
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kentucky
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Family Getaway! Fish, Hike, Swim, No Cleaning Fee
Our home is located out in country just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) & Mammoth Cave (55 min). We are surrounded by rolling hills of farmland and horse ranches. It is a log cabin style home on 30 acres. Sit out on the front porch and watch the deer. Play games, read a book. Lay out by the pool (summer). Take a hike or go fishing down at the pond. Get out and explore! Or, you can just rest and relax.

Art Studio at Turtle Hill, 5-Acre Oasis Near City
The Art Studio at Turtle Hill is located in Dayton, Ky, 2.2 miles from downtown Cincinnati. The studio is situated on 5 acres overlooking the Ohio River. The main house has a heated enclosed pool that is available to guests, a fire pit and pond. The studio has a full laundry, full kitchen and 4 off-street parking spots. The main bedroom (one queen) is on the first floor and the second bedroom (2 twins) is a loft. No cleaning fee. The studio is not suitable for children under 12. No pets please.

Life is Better On The River
Make lasting memories at this unique and family-friendly cottage on the Kentucky River. Enjoy nature at its best, along with all the comforts of home. With a pool, hot tub, and putting green there is plenty to do to unwind. Guests return year after year. This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations to reduce encounters. You will also enjoy the songs of many birds, glow of lightening bugs, and seeing the stars.

Bourbon Trail Summer POOL-ZONE! GameRm! Fish!
This two-story country-side home is sure to keep you entertained while also having a relaxing vibe for your getaway. Nestled just off the Bourbon Trail, Makers Mark and historic Bardstown are just a short drive. Proximity to Louisville and Lexington is great too! Sitting on 3 acres, this home Features 4 bedrooms, 2 and a half bathrooms! Amenities include a newly constructed fenced in Inground Pool(open April-October), WiFi/DirecTV, Pool Table, Ping Pong Table, and Golden Tee Arcade Machine!

The Enchanted Hideaway /Pet Friendly with Hot Tub!
Come relax at the Enchanted Hideaway Cabin just minutes from beautiful Lake Cumberland within the gated Lake Cumberland Resort. This 2 BR 2BA cabin offers much to love including open concept kitchen, dining, and living room area, washer and dryer, screened-in porches, grill, fire pit and much more! And you will love the private hot tub on the back porch! There are 3 community swimming pools in the resort with one only a short walk from the cabin. Book your perfect get-a-way today!

Guest House Monte Cassino Vineyards
The Guest House at Monte Cassino Vineyard, an architectural gem. At 650 sq ft, this free standing, studio loft space is a ground up restoration of an 1830s summer kitchen. Completed for 2016 season, it includes a kitchenette, with mini fridge, microwave and coffee machine. Outdoor grill is available as well. The living room has a fireplace and the bedroom loft is a designer's dream. Adjacent to the main house, the GH also includes use of the pool in season. Extremely private grounds.

Creekside Adventures
Make some memories at this unique and family-friendly place. Our guest suite is very spacious and open. Many of our guest have let us know how inviting and relaxing it is to stay in. We also have a creek where our children use to play when they were little. Kids can easily play in it when the weather is nice but please be careful on the walls and stones. We also have a pool area that is available for swimming during late May through early September. We do not allow pets. No Parties

Lake Front w/ Pool! Between Ark & Creation Museum.
If you are looking to experience lake life, look no further! Our Guest House sits on the beautiful 140 acre Bullock Pen Lake. It's a great place to relax, or enjoy kayaking, paddle boating, paddle boarding and fishing. We have one of the best views of the lake. The Guest House is fully renovated and decorated with relaxation in mind. It has everything you would need for your stay. After all, the lake is where your worries fade and memories are made! (The pool is now closed!)

God's Country
Property is a ranch style house with wood siding, nestled against a hillside with a private setting. This property offers a large yard with a in-ground pool as well as a large front porch. There are two patio areas in the back with a built in grill station and a fire-pit to enjoy on those cool evenings. The house boasts six bedrooms, open concept living room, kitchen, and dining room area with gas fireplace, and large family room.Please enter the correct number of guest

Red River Gorge. Indoor Pool. Game room. Pets.
Nestled in the quiet town of Stanton, Kentucky; 10-15 minutes away from all that Red River Gorge has to offer. 45 min to Lexington. Our house is whimsical and spacious. Perfect for families! We have a huge kitchen to cook a meal and relax by the fire pit in our private courtyard that overlooks the mountains. Also our Private pool is available March-Nov. Pet friendly (3 pet max) with a fully fenced in back yard. Please add pets to the reservation and pay the pet fee.

Cozy Cumberland Lakeview Shangri-la
A fun, lake view lake house situated on the banks of the Big South Fork River. You will love waking up each morning with a beautiful view of the river. Watch as the boats go out for a day on the water. Every where you turn, you are surround with beauty. We back up to the Daniel Boon National Forest. No matter the time of year you decide to stay, there is always plenty of hiking, fishing and site seeing to do. We are also right across the street from the pool.

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.
Popular amenities for Kentucky rentals with a pool
House rentals with a pool

Heated Pool Estate • 5 King Beds • No Bad Rooms

Cliff House

Gorgeous Lake House with Pool - Stone Haven

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

POOL/ game room! 6 beds 2 baths

Fantastic Kentucky Lake Vacation

Kentucky Sunrise 18- Greet the Sun As it Rises (Di

Tranquility in the Mountains - House
Apartment rentals with a pool

Woodson Bend Gorgeous Lake View Condo First Floor

Relaxing Cumberland Getaway

Whispering Pines Condo~Pool ~ Beach ~ Lake Rentals

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

Gated Golf Course Condo w/view of Lake Cumberland

Lakefront Condo at Woodson Bend Resort

Luxury Apartment/Near Louisville/EV Charger

A Glimpse of the Lake (77-3) Golf Pool Pickleball
Other holiday rentals with a pool

*New! *Dock! Pool! *Hot Tub! *Games! *Sleeps 18! *

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Bourbon Stave Lakehouse | Hot Tub • Deck • Cozy

4 bedroom, private pool 8 person hot tub

Derby Weekend Stay: Speakeasy + Spa + Dog Friendly

The Bell House

Heart of Richmond

Lakefront Getaway | Pool, Pickleball, Dock
Destinations to explore
- Lakehouse rentals Kentucky
- Farm stay rentals Kentucky
- Rentals with lake access Kentucky
- Beachfront rentals Kentucky
- Guest house rentals Kentucky
- Private suite rentals Kentucky
- Cabin rentals Kentucky
- Rentals with a hot tub Kentucky
- Serviced apartment rentals Kentucky
- Rentals with a fireplace Kentucky
- Pet-friendly rentals Kentucky
- Rentals with a patio Kentucky
- Tiny house rentals Kentucky
- Rentals with a washing machine and dryer Kentucky
- Villa rentals Kentucky
- Treehouse rentals Kentucky
- Rentals with beach access Kentucky
- Cottage rentals Kentucky
- Tent rentals Kentucky
- Rentals with outdoor seating Kentucky
- Barn rentals Kentucky
- Hotel rooms Kentucky
- Rentals with an accessible-height bed Kentucky
- Motorhome rentals Kentucky
- Chalet rentals Kentucky
- Rentals with an accessible-height toilet Kentucky
- Rentals with a kayak Kentucky
- Bed and breakfasts Kentucky
- Rentals with breakfast Kentucky
- Loft rentals Kentucky
- Apartment rentals Kentucky
- Townhouse rentals Kentucky
- Boutique hotels Kentucky
- House rentals Kentucky
- Smoking-friendly rentals Kentucky
- Rentals with a sauna Kentucky
- Rentals with a firepit Kentucky
- Fitness-friendly rentals Kentucky
- Aparthotel rentals Kentucky
- Holiday home rentals Kentucky
- Flat rentals Kentucky
- Dome rentals Kentucky
- Waterfront rentals Kentucky
- Rentals with an EV charger Kentucky
- Campsite rentals Kentucky
- Yurt rentals Kentucky
- Rentals with a cinema Kentucky
- Nature eco lodge rentals Kentucky
- Family-friendly rentals Kentucky
- Rentals with pools United States
- Things to do Kentucky
- Food and drink Kentucky
- Art and culture Kentucky
- Things to do United States
- Entertainment United States
- Sports activities United States
- Sightseeing United States
- Food and drink United States
- Wellness United States
- Art and culture United States
- Nature and outdoors United States
- Tours United States




