Best Vacation Homes in Midway
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $149/Night
For 7 Nights US $1,042
3239.94 ft²
7 Guests
4 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Parking
- Internet
US $253/Night
For 7 Nights US $1,771
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $329/Night
For 7 Nights US $2,306
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $270/Night
For 7 Nights US $1,891
1001.04 ft²
6 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $360/Night
For 7 Nights US $2,518
1600 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $299/Night
For 7 Nights US $2,090
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $377/Night
For 7 Nights US $2,637
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $263/Night
For 7 Nights US $1,842
Midway Luxury Rentals
6000 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $3,049/Night
For 7 Nights US $21,342
4863 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Spa
US $1,466/Night
For 7 Nights US $10,263
8000 ft²
12 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,433/Night
For 7 Nights US $10,032
3500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
US $1,158/Night
For 7 Nights US $8,103
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $1,025/Night
For 7 Nights US $7,177
2400 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $847/Night
For 7 Nights US $5,929
301.39 ft²
1 Bathroom
Free Cancellation
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
US $601/Night
For 7 Nights US $4,207
6 Guests
3 Bedrooms
3 Bathrooms
Pet Friendly
House
- Pet Friendly
- Air Conditioner
- Internet
US $591/Night
For 7 Nights US $4,134
Midway Pet Friendly Vacation Rentals
1000 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $471/Night
For 7 Nights US $3,299
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $278/Night
For 7 Nights US $1,946
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $487/Night
For 7 Nights US $3,411
9 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $526/Night
For 7 Nights US $3,680
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $294/Night
For 7 Nights US $2,055
1000 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $305/Night
For 7 Nights US $2,134
2500 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $244/Night
For 7 Nights US $1,706
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $343/Night
For 7 Nights US $2,398
Midway Large Vacation Homes
2000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
House
US $530/Night
For 7 Nights US $3,712
3000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Spa
- Fireplace/Heating
US $1,134/Night
For 7 Nights US $7,938
4863 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $1,080/Night
For 7 Nights US $7,560
Why Choose Rent By Owner for your Midway 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 Midway
When should you plan your Vacation Rentals stay?
Finding the ideal time to visit here can enhance your experience, as seasonal variations in the region’s climate and events offer different opportunities for enjoying your stay in Midway, Kentucky.
Peak Season Highlights
Spring (March to May)
During spring, the region experiences pleasant weather that is ideal for exploring outdoor activities and enjoying the scenic beauty of this destination.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Autumn brings cooler temperatures and vibrant foliage, making it a popular time for visitors seeking a tranquil retreat in this area.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
Summertime can be hot and humid here, but it also offers longer daylight hours perfect for outdoor adventures and enjoying the lively atmosphere.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
Winter tends to be quieter with colder weather, making it an ideal time for those seeking a peaceful getaway away from peak crowds.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for Midway
How to Book Your Midway 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 Midway
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 areas to prepare meals amid scenic surroundings.
- Take advantage of spacious patios or decks for relaxing outdoors.
- Make the most of private gardens or lush yards for leisurely strolls.
- Benefit from access to nearby parks or green spaces for outdoor activities.
- Utilize outdoor seating areas perfect for social gatherings or quiet evenings.
- Explore the region’s trails and scenic routes directly from your rental’s doorstep.
- Relax in outdoor fire pits or fireplaces to unwind after a day of exploring.
Top Attractions Around Midway
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities and local attractions that showcase the region’s natural beauty and southern hospitality, making it an ideal destination for a relaxing and memorable getaway.
Family Activities
- Kentucky Horse Park: Discover interactive exhibits and horseback riding experiences at this renowned equestrian park, just a short drive from your cozy vacation rental in the area.
- Midway Underground Railroad Museum: Explore the history of the region's role in the Underground Railroad through engaging exhibits designed for families visiting here.
- Bluegrass Scenic Drive: Enjoy a family-friendly scenic drive through the rolling hills and lush farmland, perfect for a relaxing day trip from your Midway accommodation.
- Local Farmers Markets: Visit nearby markets to experience fresh regional produce and handcrafted goods, offering a taste of the area's authentic local culture during your family stay.
Adult Activities
- Visit Midway's Historic Downtown: Stroll through the charming district to explore local shops, dine at quaint cafés, and enjoy the authentic small-town atmosphere.
- Explore the Horse Farm Tours: Discover the region's rich equestrian heritage by touring renowned horse farms that highlight Kentucky’s famous thoroughbred industry.
- Enjoy a Day at Whitaker Bank Ballpark: Catch a lively minor league baseball game in this vibrant sports venue nestled within the area, perfect for an entertaining evening out.
- Hike Local Nature Trails: Immerse yourself in the scenic beauty of nearby outdoor trails, offering peaceful environments and picturesque views for outdoor enthusiasts.
Other Places to Stay in Midway, KY
Damselfly Gallery
Equus Run Vineyard & Winery
Midway Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining experiences: Take advantage of the region’s charming eateries to enjoy authentic flavors that showcase the area's culinary traditions.
- Plan outdoor activities: The rural surroundings provide perfect opportunities for scenic walks, hiking, or cycling to immerse yourself in the natural beauty here.
- Visit nearby attractions: Make sure to check out the key sights within easy reach to enhance your stay and discover what makes this destination unique.
- Choose strategic accommodation options: Selecting a well-located vacation rental can maximize your convenience and allow you to experience the best of the region effortlessly.
Transportation Options
- Midway Transit Service: This reliable shuttle service offers convenient transportation around the area, making exploring your vacation rental and nearby attractions effortless.
- Local Taxis: Taxi services in the region provide quick and direct routes to key destinations, ensuring you can easily access popular spots during your stay.
- Rental Cars: Car rental agencies are available nearby, giving you the flexibility to explore the scenic surroundings at your own pace.
- Public Buses: The regional bus system connects Midway with surrounding cities and transport hubs, making it a budget-friendly option for getting around the area.
Local Customs Options
- Southern Hospitality: When visiting here, you’ll notice a warm and welcoming attitude that embodies the region’s friendly community spirit.
- Historical Appreciation:** Respect for historic landmarks and local stories is deeply ingrained, offering insights into the area's rich past.
- Community Events:** Participating in seasonal festivals and gatherings is common, highlighting the area's vibrant local culture and community bond.
Frequently Asked Questions About Midway?
1. What are the top vacation rentals in Midway?
There are a lot of options in Midway. If you plan on staying in the Midway area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Midway:
- Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery
- Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country
- Experience horse park fun , the Bourbon Trail and a golf course out your door!
- Bit and Bourbon
- Stunning Horse Farm Experience on Bourbon Trail!
- Family-friendly newly built house in the heart of Kentucky's Horse Country
- Springwood Cottage in the Heart of the Bluegrass
- Discover Your Perfect Getaway: Cottage in the Heart of Horse & Bourbon Country!
- Loft above Beautiful Horse Barn on Bourbon Trail
- Cozy cabin in the heart of horse country
2. Which vacation homes in Midway are best for families?
If you are looking for a family-friendly vacation home in Midway, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Midway:
3. How many Rentbyowner vacation rentals are available in Midway?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 73 in the Midway 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 Midway.
4. What is the cancellation policy for vacation rentals in Midway, Kentucky?
Cancellation policies vary by property; it is recommended to review the specific rental listing for detailed terms or contact the host directly to understand the options available.
5. How do I confirm my booking at a vacation rental in Midway, Kentucky?
Booking confirmation typically occurs after completing the reservation process and receiving a confirmation email from the property owner or manager. Be sure to check your inbox for confirmation details.
6. Are there any house rules I should be aware of when staying in a vacation rental here?
House rules differ between properties, so it's important to read the listing carefully. If you have questions about specific rules, reaching out to the host ensures a smooth stay.
7. What amenities are generally included with vacation rentals in this destination?
Amenities can vary, but most rentals offer essentials such as Wi-Fi, parking, and kitchen facilities. Review the property listing for exact amenities offered before booking.
8. Is there a minimum stay requirement for booking vacation rentals in the region?
Minimum stay requirements depend on the property and season. Check the listing details or contact the owner directly to confirm the length of stay needed.
Midway Top Rated Vacation Rentals
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $553/Night
For 7 Nights US $3,870
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $125/Night
For 7 Nights US $873
333.68 ft²
5 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $134/Night
For 7 Nights US $938
US $142/Night
For 7 Nights US $992
9 Guests
1 Bedroom
3 Bathrooms
Family Friendly
Other
- Private Pool
- Fireplace/Heating
- Pool
US $568/Night
For 7 Nights US $3,975
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Pool
- Balcony/Terrace
- Pet Friendly
US $200/Night
For 7 Nights US $1,400
