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  3. Louisville
  4. Crestwood
  5. Rentals by Owner

Discover Your Perfect Crestwood Rentals by Owner

Crestwood Rentals by Owner

More Top-Rated Rentals by Owner in Crestwood Area

Why Choose Rent By Owner for your Crestwood vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, as understanding seasonal trends in this destination helps you find the perfect rental by owner through Rent By Owner for a memorable stay.

Peak Season Highlights

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Spring (March to May)

During spring, you can enjoy mild temperatures and the region's natural beauty while visiting Crestwood, Kentucky. This is an ideal time for outdoor activities and exploring the local area.

Average Temperature Daytime: 65°F - Nighttime: 45°F
autumn
Fall (September to November)

Autumn brings comfortable weather and vibrant foliage, making it a popular season for visitors seeking a scenic experience here. The region’s landscape transforms beautifully during this time of year.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

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Summer (June to August)

Summer offers warmer weather perfect for relaxing in your rental and enjoying the longer days. While it can be busier, it remains a favorable season for visiting Crestwood.

Average Temperature Daytime: 85°F - Nighttime: 65°F
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Winter (December to February)

During winter, the area experiences cooler temperatures with a quieter atmosphere, making it suitable for those seeking a peaceful getaway. Winter also provides a cozy ambiance for your stay.

Average Temperature Daytime: 40°F - Nighttime: 25°F

Weekly Weather Forecast for Crestwood

How to Book Your Crestwood vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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

More Top-Rated Rentals by Owner in Crestwood Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 seating areas perfect for relaxing or entertaining guests amidst the scenic surroundings.
  • Take advantage of private patios or decks that offer a great spot to enjoy morning coffee or evening sunsets.
  • Make use of landscaped gardens or yard space for outdoor activities and family fun.
  • Benefit from access to well-maintained walking trails or pathways nearby to explore the natural beauty of the region.
  • Experience outdoor grilling stations or barbecue pits for preparing meals while enjoying the fresh air.
  • Utilize community pools or swimming areas available within this destination for refreshing dips on warm days.
  • Capitalize on scenic viewpoints or lookout spots that showcase the area's picturesque landscapes from your rental.

Top Attractions Around Crestwood

What attractions are nearby?

Within the area, you can enjoy a variety of outdoor activities and local attractions that showcase the charm of this destination, making your stay here both relaxing and memorable.

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Family Activities

  • Crestwood Nature Park: Enjoy a family picnic and explore walking trails that showcase the natural beauty of this destination's outdoor space.
  • Plantation Agriculture Museum: Discover interactive exhibits about local farm life and history, making it an educational outing for children and adults alike.
  • O'Connell Family Farm: Experience seasonal activities such as pumpkin picking or hayrides, perfect for creating memorable family moments during your stay here.
  • Local Community Events: Participate in seasonal festivals and family-friendly gatherings that highlight the welcoming spirit of this region.
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Adult Activities

  • Golfing at Sunset Hills Country Club: Enjoy a relaxing round of golf at this nearby club, perfect for unwinding and taking in scenic views.
  • Exploring Downtown Crestwood’s Local Shops and Cafes: Discover charming local boutiques and cozy cafes that offer a taste of the area's welcoming community atmosphere.
  • Visiting the Kentucky Derby Museum in Louisville: Immerse yourself in American horse racing history and experience world-renowned attractions just a short drive away.
  • Hiking at Jefferson Memorial Forest: Take advantage of the expansive trails here to enjoy nature and outdoor activities in a peaceful setting close to the region.

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Crestwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and shopping options: Take advantage of the area's charming boutiques and eateries to enjoy an authentic taste of the region during your stay.
  • Plan outdoor activities nearby: Engage in scenic parks or recreational spots close to your rental to make the most of the natural beauty here.
  • Connect with hosts for personalized tips: Reach out to your rental owner for insider recommendations on hidden gems and must-see spots in the area.
  • Check local event calendars: Stay informed about festivals, markets, or community events happening during your visit for a richer experience here.

Transportation Options

  • Louisville International Airport: This major airport provides convenient domestic flights and ground transportation options for travelers arriving or departing from the area.
  • Local Taxi Services: Reliable taxi providers operate throughout the region, offering comfortable and direct transportation to Crestwood and surrounding destinations.
  • Ride-Sharing Services: Popular ride-sharing companies are readily available here, providing flexible and affordable travel options within the area.
  • Public Transit Systems: Local bus routes connect Crestwood with nearby cities, making it easy to explore the region without a private vehicle.

Local Customs Options

  • Southern Hospitality: Visitors often find the warm and welcoming attitude of local residents a notable aspect of this region, reflecting its friendly community spirit.
  • Farmers' Market Traditions: Engaging with neighborhood farmers' markets offers insight into the area's agricultural roots and local produce in this part of Kentucky.
  • : If you attend any racing events nearby, you'll notice a strong appreciation for horse racing customs that are cherished here in the region.
  • Festive Holiday Celebrations: The area hosts traditional seasonal festivities that highlight local culture, making it an enjoyable experience for visitors staying in private rentals.

Frequently Asked Questions About Crestwood Rentals by Owner

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:

2. How many Rentbyowner vacation rentals are available in Crestwood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 65 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. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary depending on the individual listing. It’s recommended to review the specific rental’s cancellation terms on the listing page or contact the owner directly for detailed information.

4. How do I contact the owner before booking to ask questions about the property?

You can reach out to the owner through the messaging system provided on the rental platform. This allows you to ask any questions regarding the property, amenities, or stay details before finalizing your reservation.

5. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning, service charges, or security deposits are often listed on the property details page. Always read the full listing description or contact the owner for clarification on any extra costs.

6. What amenities are typically included in a rental by owner in this region?

Most rentals offer essential amenities like Wi-Fi, parking, and kitchen facilities. However, specific features can vary, so it’s best to check the listing for a comprehensive list of what is included during your stay.

7. Is there a minimum stay requirement for rentals in this destination?

Minimum stay requirements differ by listing; some may require stays of several nights, while others might be flexible. Review each listing’s policies or contact the owner directly if you have specific dates in mind.

More Rentals You May Like Near Crestwood

More Top-Rated Rentals by Owner in Crestwood Area