Holiday rentals with a pool in Estill County

Pool - Hot Tub - Theater - Arcade - Mural - RRG

Sunlight spills across rich wood interiors, the scent of pine lingers in the air. Whether you’re gathered around the fire pit under a blanket of stars or soaking in the hot tub after a day of adventure, The Grey House is made for moments you’ll never forget. This spacious cabin blends rustic charm w/ modern comfort. Bring your four-legged family members along! Spend mornings sipping coffee on the porch, afternoons splashing in the pool, & evenings cooking together in the fully equipped kitchen.

Location · Family · Air conditioning

Heated Pool! Hatton Hideaway at Red River Gorge

Experience luxury on 20+ private acres near Red River Gorge. This 3,310 sq ft estate features 4 bedrooms, 2.5 baths, 2 elegant family rooms, a private inground pool, hot tub, arcade, and a tranquil pond. Thoughtfully designed for upscale comfort and unforgettable gatherings, it’s just minutes from Natural Bridge State Park and Red River Gorge. A premier getaway blending refinement and nature. Weather conditions can affect quality of the pool and hot tub and owner cannot assume responsibility.

Location · Family · Bathroom

The Wildwood RV Rental @ Callies

Hosted by Destination Unknown RV Rentals. Enjoy comfort in our 2021 Forest River Wildwood Heritage Glen. RV features 2 bedrooms—one with a king suite and walk-in closet, the other with bunk beds—plus a queen loft and pull-out sofa to sleep up to 8. Enjoy a spacious kitchen with XL pantry, large island, huge fridge with wine cooler, and XL sink. Relax by the fireplace, stay cool with powerful A/C, and refresh in the walk-in shower. Delivered, leveled, and fully set up—just arrive and unwind!

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

Family · Location · Wi-Fi

The Lodge 3 bedroom 2 bath barndo in wooded area

Enjoy the sounds of nature when you stay in this unique place. Beautifully located in the middle of 40 acres surrounded by trees and wildlife.  Spacious living area and large lighted patio makes this ideal for family and friend gatherings. A kitchen equipped with everything you need to entertain. Gorgeous view of the mountains at your private fire pit. Also on the property is a shared hot tub and pool…. Firewood available at a small fee. All that’s missing is you bring your cooler!!

Location · Family · Sleep quality

Hemlock Hideaway Red River Gorge Recent Refreshed

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.

Value · Family · Beach

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.

Value · Family · Hiking

Stargazer - Rooftop + Hot Tub + Walk to Red River

Escape to Red River Gorge at our Stargazer Cabin, just 15 minutes from Natural Bridge, hiking trails, and world-class rock climbing. Relax on the rooftop stargazing deck with the smart phone enable telescope or by the cozy gas fireplace after a day of adventure. Walk just half a mile to the Red River, or grab a bite at Miguel’s Pizza, a local favorite. Whether you're hiking, climbing, or unwinding, this is the perfect basecamp for your Red River Gorge getaway!

Family · Location · Cleanliness

Premium A-Frame • Hot Tub • Sauna • Pond & Animals

Private 58-acre A-Frame retreat in the Kentucky Appalachians with mountain views, a stocked fishing pond, hot tub, infrared sauna, fire pit, games, and rare farm animals. Meet Suffolk Punch draft horses, a Highland cow and calf, and Thoroughbreds by request. No TV by design, just nature, stillness, connection, and a true farm-stay experience. Sleeps 7. Designed for families, couples and friends seeking nature, privacy and unforgettable memories.

Location · Value · Parking

Mountain Retreat | Pool, Pond, Views & Wi-Fi

Escape to a secluded luxury mountain retreat on 840 private acres where peace and adventure meet. Relax in a private pool, fish in the stocked pond, or unwind in the sunroom surrounded by nature. Enjoy a playground for kids, cozy campfires under the stars, and an optional upgrade of 12 full hook-up campsites for groups. Just 30 minutes from Red River Gorge and Natural Bridge. Pool opens Memorial Day weekend and closes Sept; weather-dependent.

Location · Family · Cleanliness

The Wildcat RV Rental @ Callies

Hosted by Destination Unknown RV Rentals. Stay in our spacious 2022 Wildcat fifth wheel at Callie’s Lake and Campground near Red River Gorge. It features 2 bedrooms, a king bed with walk-in closet, private bunk room, queen loft, and multiple pull-outs—sleeping up to 8. Enjoy a full kitchen, walk-in shower, dual Lazy Boys, massaging loveseat, cold A/C, and two awnings. Set up and ready when you arrive! Campground site must be booked separately.

The Outback RV Rental @ Callies

Hosted by Destination Unknown RV Rentals. Experience comfort in our 2018 Keystone Outback at Callie’s Lake and Campground near Red River Gorge. Sleeps 7–8 with a king bed, bunk room, queen pull-out, and walk-in shower. Enjoy the heated fireplace, cold A/C, and plenty of space to relax after hiking or exploring. Set up and ready when you arrive—just bring your adventure gear and settle in!