Kentucky Winter Rental
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $199/Night
For 7 Nights US $1,395
393.65 ft²
18 Guests
8 Bedrooms
7 Bathrooms
Free Cancellation
Bed & Breakfast
- Oceanfront
- Hot Tub
- Spa
US $391/Night
For 7 Nights US $2,737
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Hot Tub
- Spa
- Fireplace/Heating
US $361/Night
For 7 Nights US $2,527
950 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pool
US $209/Night
For 7 Nights US $1,463
258.33 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Free Cancellation
Bed & Breakfast
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $296/Night
For 7 Nights US $2,070
425 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $101/Night
For 7 Nights US $710
1496.18 ft²
6 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $324/Night
For 7 Nights US $2,269
950 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $138/Night
For 7 Nights US $965
1076.39 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $157/Night
For 7 Nights US $1,100
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $198/Night
For 7 Nights US $1,387
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Pet Friendly
- Parking
- Air Conditioner
US $127/Night
For 7 Nights US $887
1042 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $249/Night
For 7 Nights US $1,744
Why Choose Rent By Owner for your Kentucky Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Kentucky
How to Book Your Kentucky Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Kentucky
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Kentucky, KY
Louisville
Jefferson County
Lexington
Lebanon
Marion County
Fayette County
Paducah
Downtown Louisville
Downtown
Lake Barkley
West Main Historic District
Northside District
Kentucky Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Kentucky?
There are a lot of options in Kentucky. If you plan on staying in the Kentucky area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Kentucky:
- Secluded Red River Gorge Pet-Friendly Cabin on 6 acres
- Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!
- A Cozy Cottage Near the Heart of All Louisville Attractions!
- YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
- Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed
- Cumberland River Cabin Rental
- 2 or 3 Bedroom/Baths House in Andover Convenient to All of Lexington
- BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
- The Kentucky Kajun! A Beautiful 5 Bed/4 Bath Cabin On Barren River Lake.
- Renovated Train Station on Thoroughbred Horse Farm
2. How many Winter Rentals are available in Kentucky?
Currently, the total number of properties listed by RBO in 2026 is over 6886 in the Kentucky area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Kentucky.
More Rentals You May Like Near Kentucky
2249.66 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Pool
US $179/Night
For 7 Nights US $1,253
2000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $309/Night
For 7 Nights US $2,161
1 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $157/Night
For 7 Nights US $1,099
768 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $143/Night
For 7 Nights US $1,002
750 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $204/Night
For 7 Nights US $1,431
1230 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Spa
- Fireplace/Heating
US $236/Night
For 7 Nights US $1,651
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $148/Night
For 7 Nights US $1,034
600 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $158/Night
For 7 Nights US $1,105
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $256/Night
For 7 Nights US $1,794
432 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $173/Night
For 7 Nights US $1,209
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $219/Night
For 7 Nights US $1,533
1000 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $165/Night
For 7 Nights US $1,158
