Best Vacation Homes in Kentucky
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R2,800/Night
For 7 Nights ZA R19,599
1295.26 ft²
25 Guests
6 Bedrooms
9 Bathrooms
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
ZA R3,316/Night
For 7 Nights ZA R23,205
646 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Parking
- Air Conditioner
ZA R5,437/Night
For 7 Nights ZA R38,052
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R2,589/Night
For 7 Nights ZA R18,125
495.14 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Parking
- Air Conditioner
- Internet
ZA R2,114/Night
For 7 Nights ZA R14,798
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R5,143/Night
For 7 Nights ZA R36,003
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R3,267/Night
For 7 Nights ZA R22,861
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R4,679/Night
For 7 Nights ZA R32,759
Kentucky Luxury Rentals
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Unlock the Best Price
3300 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Unlock the Best Price
1500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Unlock the Best Price
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
Unlock the Best Price
16146 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Unlock the Best Price
1500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Unlock the Best Price
16146 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Unlock the Best Price
12 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
ZA R163,875/Night
For 7 Nights ZA R1,147,125
Kentucky Pet Friendly Vacation Rentals
384 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R2,863/Night
For 7 Nights ZA R20,042
ZA R2,704/Night
For 7 Nights ZA R18,928
1 Bedroom
1 Bathroom
Couples Retreat
Cabin
- Balcony/Terrace
- Pet Friendly
- Parking
ZA R4,675/Night
For 7 Nights ZA R32,726
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R2,420/Night
For 7 Nights ZA R16,945
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Pet Friendly
- Parking
- Air Conditioner
ZA R2,075/Night
For 7 Nights ZA R14,536
600 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R2,588/Night
For 7 Nights ZA R18,108
432 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
ZA R2,830/Night
For 7 Nights ZA R19,812
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R1,508/Night
For 7 Nights ZA R10,554
Kentucky Large Vacation Homes
1798 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R4,138/Night
For 7 Nights ZA R28,973
393.65 ft²
18 Guests
8 Bedrooms
7 Bathrooms
Free Cancellation
Bed & Breakfast
- Oceanfront
- Hot Tub
- Spa
ZA R6,408/Night
For 7 Nights ZA R44,853
12 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Spa
- Fireplace/Heating
ZA R3,794/Night
For 7 Nights ZA R26,564
1900 ft²
11 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R4,893/Night
For 7 Nights ZA R34,250
258.33 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Free Cancellation
Bed & Breakfast
- Spa
- Fireplace/Heating
- Balcony/Terrace
ZA R4,845/Night
For 7 Nights ZA R33,922
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
ZA R4,217/Night
For 7 Nights ZA R29,514
936 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R4,589/Night
For 7 Nights ZA R32,120
1100 ft²
10 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R3,671/Night
For 7 Nights ZA R25,696
Why Choose Rent By Owner for your Kentucky Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit Kentucky
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can enhance your experience and ensure you enjoy the region's natural beauty and local events at their best, making it ideal to plan your stay according to seasonal weather patterns and regional festivities.
Peak Season Highlights
Spring (March to May)
During spring, the region comes alive with blooming flowers and mild weather, making it an ideal time to explore outdoor activities near your vacation rentals.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Autumn offers vibrant foliage and comfortable temperatures, perfect for enjoying the scenic landscapes from your holiday home.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
While summer can be lively, it’s also when some travelers seek quieter stays in the area’s cozy vacation rentals due to the higher temperatures and bustling crowds.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
Winter (December to February)
This is the quietest time of year, offering a peaceful retreat where you can enjoy the region’s charm without the typical tourist crowds.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for Kentucky
How to Book Your Kentucky Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy outdoor grilling and dining on the patio or deck, perfect for making the most of warm Kentucky evenings.
- Take advantage of private or community swimming pools to relax and cool off during your stay.
- Explore scenic walking or hiking trails directly from the property, allowing you to immerse yourself in the natural beauty of the area.
- Make use of outdoor fire pits for cozy evenings under the stars with friends or family.
- Benefit from spacious yards or gardens ideal for outdoor activities, picnics, or playing with children or pets.
- Access to tennis courts, basketball hoops, or other sports facilities may be available for active pursuits.
- Relax in outdoor lounging areas or hammocks designed for unwinding while enjoying the fresh air of this destination.
Top Attractions Around Kentucky
What attractions are nearby?
Within close proximity to your Kentucky vacation rental, you can explore a variety of outdoor activities, cultural experiences, and scenic attractions that showcase the best of this region's natural beauty and local heritage.
Family Activities
- Kentucky Kingdom & Race Track: Enjoy a fun-filled day at this popular amusement park and race track, perfect for family adventures amid thrilling rides and live entertainment.
- The Kentucky Derby Museum: Discover the rich history of the legendary horse race with interactive exhibits and guided tours that engage all ages here in the region.
- Louisville Zoo: Explore the diverse animal exhibits and take part in engaging educational programs designed to entertain and inform young visitors in this area.
- Bourbon Trail Family Tours: Experience family-friendly tours along the famous Bourbon Trail, where you can learn about Kentucky’s heritage in a relaxed and enjoyable setting.
Adult Activities
- Touring the Bourbon Trail: Discover the rich heritage of Kentucky’s bourbon industry by visiting renowned distilleries and experiencing guided tastings along this famous trail.
- Exploring Horse Country: Immerse yourself in the world of thoroughbred racing and visit historic horse farms that showcase the region’s deep-rooted equestrian culture.
- Enjoying Scenic River Activities: Take advantage of kayaking, paddleboarding, or relaxing cruises on the area's picturesque rivers and lakes nestled within the landscape.
- Hiking and Nature Walks: Explore scenic trails and natural parks that offer breathtaking views and a tranquil escape into the region’s diverse wilderness.
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 Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Sample the region’s renowned dishes at local eateries to truly experience the authentic flavors of Kentucky while enjoying the comfort of nearby vacation rentals.
- Visit Year-Round Attractions: Take advantage of the area's diverse seasonal attractions, which can be conveniently accessed from your well-located vacation rental here, ensuring a memorable stay regardless of the time of year.
- Plan Outdoor Activities: Make the most of the scenic landscapes by engaging in outdoor pursuits such as hiking or picnicking, all within easy reach of your vacation rental in this destination.
- Check for Local Events: Stay updated on regional festivals and events that offer cultural insights and entertainment, providing an enriching experience during your stay in the area.
Transportation Options
- Interstate Highway System: You can conveniently travel across the region via major interstate highways, providing quick access to popular destinations within Kentucky.
- Regional Airports: Several regional airports in this area offer domestic flights, making it easy to arrive and depart without long drives from larger hubs.
- Rail Services: Modern rail options connect key cities and towns, offering a scenic and relaxing alternative for exploring the region's attractions.
- Public Transit Systems: Local bus services and transit options are available in urban centers, ensuring affordable transportation while staying near your vacation rental.
Local Customs Options
- Horse Racing Etiquette: When visiting here, you’ll notice that horse racing is a cherished tradition, and showing respect during races is an important part of the local customs.
Embrace the region’s rich musical heritage by participating in or enjoying bluegrass performances, which are a vital aspect of the area's cultural identity. - Southern Hospitality: Expect a warm welcome and courteous interactions, as friendliness and politeness are deeply rooted in the local way of life in this destination.
- Local Food Traditions: Sampling regional dishes like bourbon-glazed favorites or traditional country cooking is customary, reflecting the area's culinary customs.
Frequently Asked Questions About Kentucky?
1. What are the top vacation 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 Vacation 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
- Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
- The Kentucky Kajun! A Beautiful 5 Bed/4 Bath Cabin On Barren River Lake.
2. How many vacation rentals have private pools in Kentucky?
There are 538 vacation rentals with private pools near Kentucky. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Kentucky are best for families?
If you are looking for a family-friendly vacation home in Kentucky, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Kentucky:
4. How many Rentbyowner vacation rentals are available in Kentucky?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 14905 in the Kentucky area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Kentucky.
5. What is the cancellation policy for vacation rentals in Kentucky?
Each listing has its own cancellation policy, which can range from flexible to strict. You should review the specific cancellation terms on the property’s page before booking or contact the owner for clarification.
6. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning, service charges, or taxes are often listed in the reservation details. Be sure to check the total cost breakdown on the listing or reach out directly to the owner for specific fee information.
7. How do I confirm my reservation and what is required at check-in?
Confirmation details and check-in instructions are provided once your reservation is complete. Many hosts require identification or security deposits; these details are typically outlined in the property description or sent via communication after booking.
8. Can I modify or cancel my booking if my plans change?
Modification and cancellation options depend on the individual listing’s policies. Always review the property's cancellation policy before booking and contact the owner directly if you need assistance with changes.
9. What amenities are typically included in vacation rentals here?
Listings usually specify available amenities such as Wi-Fi, parking, kitchens, and outdoor spaces. For detailed information about what’s included, read the property description carefully or contact the owner to ensure your needs are met.
Kentucky Top Rated Vacation Rentals
625 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Private Pool
- Hot Tub
- Fireplace/Heating
ZA R3,119/Night
For 7 Nights ZA R21,828
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R4,195/Night
For 7 Nights ZA R29,366
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R3,215/Night
For 7 Nights ZA R22,500
950 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pool
ZA R3,424/Night
For 7 Nights ZA R23,975
4000 ft²
16 Guests
8 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
ZA R15,153/Night
For 7 Nights ZA R106,060
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
ZA R5,058/Night
For 7 Nights ZA R35,413
7050 ft²
14 Guests
7 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
ZA R23,618/Night
For 7 Nights ZA R165,317
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R2,682/Night
For 7 Nights ZA R18,780
