Holiday rentals with a pool in Kentucky

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.

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

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.

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

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!.

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 OPEN!!!) 5/11/26

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

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, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

Hemlock Hideaway Red River Gorge game room hot tub

Hemlock Hideaway at Red River Gorge is a 3 bedroom, 2 bath cabin that can sleep up to 10. The cabin features a pool, hot tub, game room, and electric vehicle charger on a private 2.5 acre setting. The home has two king sized beds, three full sized beds, a twin trundle bed, twin sleeper chair and queen sleeper sofa. There is a fully stocked kitchen and free onsite laundry. All of this and so much more and only a 20 minute drive to the Red River Gorge, Natural Bridge State Park area.

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.

Whispering Woods Cottage | Hot Tub | Pool

Welcome to Whispering Woods, your peaceful sanctuary nestled near Lake Cumberland. Step into our cozy 1-bedroom cottage that offers tranquil surroundings and a restorative night's sleep after your day's adventures. Perfect for a romantic getaway, a solo retreat, or a change of scenery for remote workers, Whispering Woods provides space for up to two guests. ☆ Book your escape at Whispering Woods today to experience the enchantment of lakeside living. Your perfect retreat awaits! ☆

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.