Best Vacation Homes in Crestwood
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
8 Guests
876 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $363/Night
7 Nights - US $2,541
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
1453.13 ft²
- Parking
View
Internet
Pet Friendly
US $214/Night
7 Nights - US $1,498
Hotel
9.6(312 Reviews)
1 Bath
Breakfast- Parking
Pool- Kitchen
US $158/Night
7 Nights - US $1,104
Cottage
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $302/Night
7 Nights - US $2,111
House
9.8(6 Reviews)
2 Bedrooms
2 Baths
7 Guests
904.17 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $320/Night
7 Nights - US $2,242
Cabin
10.0(52 Reviews)
7 Bedrooms
5 Baths
20 Guests
8000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,370/Night
7 Nights - US $9,589
House
10.0(25 Reviews)
4 Bedrooms
3 Baths
12 Guests
5500 ft²
Private Pool
Hot Tub- Parking
- Pool
US $974/Night
7 Nights - US $6,820
House
10.0(17 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,858
Crestwood Luxury Rentals
Unlock the Best Price
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
6000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $4,136/Night
7 Nights - US $28,949
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,406/Night
7 Nights - US $23,841
House
10.0(6 Reviews)
5 Bedrooms
4 Baths
10 Guests
5000 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,043/Night
7 Nights - US $21,304
House
5 Bedrooms
4 Baths
10 Guests
- Internet
Child Friendly
Laundry
Bedding/Linens
US $2,838/Night
7 Nights - US $19,866
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
12 Guests
4700 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $2,595/Night
7 Nights - US $18,167
House
10.0(1 Review)
4 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,573/Night
7 Nights - US $18,013
House
5 Bedrooms
4 Baths
11 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $2,284/Night
7 Nights - US $15,990
Crestwood Pet Friendly Vacation Rentals
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $1,690/Night
7 Nights - US $11,827
Apartment
3 Bedrooms
2 Baths
6 Guests
3003.13 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $317/Night
7 Nights - US $2,221
Hotel
8.6(1009 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $112/Night
7 Nights - US $786
House
9.6(12 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $341/Night
7 Nights - US $2,384
House
1 Bedroom
1 Bath
6 Guests
1786.81 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $723/Night
7 Nights - US $5,060
House
3 Bedrooms
3 Baths
6 Guests
1790 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $420/Night
7 Nights - US $2,941
House
7.6(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $266/Night
7 Nights - US $1,863
New
Apartment
3 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Breakfast
- Balcony/Terrace
- Kitchen
US $495/Night
7 Nights - US $3,463
Crestwood Large Vacation Homes
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $535/Night
7 Nights - US $3,747
House
9.0(2 Reviews)
7 Bedrooms
4 Baths
17 Guests
9000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,043/Night
7 Nights - US $14,303
House
5 Bedrooms
4 Baths
14 Guests
7000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,576/Night
7 Nights - US $11,030
House
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,040/Night
7 Nights - US $7,277
House
9.8(82 Reviews)
8 Bedrooms
5 Baths
25 Guests
8500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,212/Night
7 Nights - US $8,482
House
10.0(9 Reviews)
5 Bedrooms
5 Baths
12 Guests
4500 ft²
- Private Pool
- Parking
- Pool
Ocean View
US $3,231/Night
7 Nights - US $22,620
House
9.0(18 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $384/Night
7 Nights - US $2,687
House
4 Bedrooms
4 Baths
10 Guests
6000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $4,783/Night
7 Nights - US $33,478
Why Choose Rent By Owner for your Crestwood 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 Crestwood
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you experience the region's best weather and local events, making your stay in Crestwood, Kentucky, unforgettable.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences mild temperatures and blooming landscapes, making it an ideal time to enjoy the region's natural beauty from your vacation rental.
Average Temperature Daytime: 60-75°F - Nighttime: 45-55°F
Fall (September to November)
Autumn brings cooler weather and vibrant foliage, providing a picturesque setting for your stay in this destination’s cozy vacation rentals.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Summer (June to August)
In summer, higher temperatures and humidity are common, offering warm weather perfect for outdoor activities while enjoying your vacation rentals here.
Average Temperature Daytime: 85-90°F - Nighttime: 65-70°F
Winter (December to February)
The winter months tend to be colder with occasional snowfall, providing a peaceful atmosphere for those seeking a quiet retreat from their vacation rentals.
Average Temperature Daytime: 40-45°F - Nighttime: 25-30°F
Weekly Weather Forecast for Crestwood
How to Book Your Crestwood 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 Crestwood
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 a private outdoor swimming pool to relax and unwind during your stay.
- Take advantage of spacious patios or decks ideal for outdoor dining and entertaining.
- Explore well-maintained lawns and gardens perfect for outdoor activities and picnics.
- Make the most of outdoor grilling areas to prepare meals with friends or family.
- Utilize shaded verandas or porches to enjoy the fresh air while staying comfortable.
- Benefit from outdoor fire pits for cozy evenings and storytelling sessions.
- Access nearby scenic walking or hiking trails that showcase the natural beauty of the region.
Top Attractions Around Crestwood
What attractions are nearby?
Nearby in this area, you can enjoy a variety of outdoor activities and explore local parks that offer scenic walking trails, making your stay in Crestwood a truly engaging experience.
Family Activities
- Creason Park: Enjoy outdoor family activities at this scenic park, perfect for picnics, playground visits, and walking trails amidst natural beauty.
- Crestwood Community Center: Participate in engaging programs and family-friendly events designed to create lasting memories in this welcoming local hub.
- Hays Kennedy Park: Explore spacious open areas, sports fields, and play zones that make it easy for families to stay active and have fun together here.
- The Great Escape Golf Course: Experience a friendly round of mini-golf tailored for all ages, offering entertainment and relaxation within the region.
Adult Activities
- Louisville Mega Cavern: Explore this underground adventure park offering zip lines, a ropes course, and tram tours that highlight the region's unique underground attractions.
- Burnett Farms Winery: Enjoy wine tastings amid scenic landscapes, showcasing the local viticulture scene just a short drive from your stay here.
- Glen Oaks Country Club: Play a round of golf at this prestigious course known for its well-maintained fairways and picturesque views in the area.
- Crestwood Community Park: Relax or engage in outdoor activities like walking, picnicking, and sports at this beloved local park near your vacation rental.
Other Places to Stay in Crestwood, KY
Open Range Sports
Yew Dell Botanical Gardens
Orchard Grass Hills
Buckner
Crestwood Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of nearby restaurants and cafes to experience the region’s unique flavors during your stay.
- Plan outdoor activities: Engage in outdoor pursuits like parks or trails to enjoy the natural beauty that surrounds this destination.
- Visit seasonal events: Check out any local festivals or markets happening here for a richer cultural experience.
- Utilize nearby amenities: Make the most of convenient shops, entertainment, and services available in the area to enhance your visit.
Transportation Options
- Private Car Rentals: Renting a car here offers the flexibility to explore Crestwood and its surrounding region at your own pace, making it an ideal option for comfortable transportation during your stay.
- Local Taxis and Rideshare Services: Taxis and rideshare options are readily available in this area, providing convenient and reliable door-to-door service for quick trips around Crestwood.
- Public Transit: Although limited, local bus services operate nearby, offering an economical way to navigate within the region without the need for personal vehicle use.
- Airport Transfers: Professional shuttle services and private transfers connect visitors to the closest airports, streamlining your journey from the moment you arrive here.
Local Customs Options
- Southern Hospitality: Visitors often notice the warm and welcoming attitude that is a hallmark of this region, making your stay in Crestwood, Kentucky, truly memorable.
When dining here, it’s common to enjoy hearty Southern-style meals that reflect the area's rich culinary traditions. - Community Events: Participating in local festivals and gatherings is a cherished way to connect with the friendly residents of this destination.
- Respect for Tradition: Respecting longstanding customs and community values can enhance your experience while exploring Crestwood and its surrounding areas.
Crestwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Crestwood?
There are a lot of options in Crestwood. If you plan on staying in the Crestwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Crestwood:
- Charming house in one of Louisville's most coveted neighborhoods
- The Persimmon Ridge Lodge - Golf Room & Pickleball!
- 3.7 Acre Estate w/Heated Pool, 5 Kings-2 Game Rms
- King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71.
- Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
- Attention Derby visitors . 5,000 Sq Ft, 5 Bedroom, 41/2 baths.
- 4Br Farm w Private Heated Pool on 25 acres ~ Bourbon Trail, Horses, Mini goats
- Bourbon Trail Getaway on Quiet Cul-de-sac - minutes from I-71 - Sleeps 8
- The Sweet Retreat Wheelchair Accessible Historic Home
- Briar Creek Cottage
2. How many vacation rentals have private pools in Crestwood?
There are 6 vacation rentals with private pools near Crestwood. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Crestwood are best for families?
If you are looking for a family-friendly vacation home in Crestwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Crestwood:
4. How many Rentbyowner vacation rentals are available in Crestwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 100 in the Crestwood 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 Crestwood.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the terms and any potential fees involved.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or local taxes are specified in each listing. Be sure to read the full description or reach out to the host for clarification before confirming your reservation.
7. How do I ensure my booking is secure when reserving a vacation rental nearby?
Secure booking is facilitated through verified listings with reliable payment options. Always confirm the listing’s authenticity and communicate through the platform to protect your personal and financial information.
8. What amenities are typically included in vacation rentals around this region?
Amenities can vary but often include essentials like Wi-Fi, parking, kitchen facilities, and comfort features. Check the individual listing for a detailed list of what’s included during your stay.
9. Is it possible to find pet-friendly vacation rentals in this destination?
Yes, many properties accommodate pets. Use the search filters to specify your requirements and review the policies listed by each host to ensure the property is suitable for your furry friends.
Crestwood Top Rated Vacation Rentals
Hotel
9.0(886 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $111/Night
7 Nights - US $778
Hotel
8.7(224 Reviews)
10 Baths
327.22 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $121/Night
7 Nights - US $845
Hotel
8.6(637 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $96/Night
7 Nights - US $669
US $94/Night
7 Nights - US $655
Hotel
8.1(73 Reviews)
8 Baths
392.88 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $162/Night
7 Nights - US $1,134
Hotel
8.0(265 Reviews)
10 Baths
500.52 ft²
- Private Pool
- Oceanfront
- Breakfast
EV Charge Station
US $100/Night
7 Nights - US $700
Hotel
7.6(401 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $107/Night
7 Nights - US $749
Hotel
7.6(142 Reviews)
6 Baths
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $98/Night
7 Nights - US $687
