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Pleasant Luxury Rentals

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Why Choose Rent By Owner for your Pleasant Vacation Rental Homes?

What makes our Vacation Rentals 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 Pleasant

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as the region offers different attractions and weather conditions that cater to various preferences throughout the year.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This is when you can enjoy the warm weather and longer days, making it ideal for exploring outdoor activities in the region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

During this period, the area offers pleasant weather and vibrant autumn foliage, perfect for sightseeing and outdoor leisure.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

You might find fewer crowds during this chilly season, with cooler temperatures ideal for cozy indoor pursuits or off-season travel deals.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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Early Spring (March to April)

As the region transitions from winter, this time offers milder weather but less activity, making it a quiet period for those seeking solitude.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Pleasant

How to Book Your Pleasant 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 Pleasant

More Top-Rated Vacation Rentals in Pleasant Area

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 dining with a fully equipped patio or picnic area, perfect for gatherings and meals under the sky.
  • Relax by a private or shared swimming pool to cool off during warm summer days in the region.
  • Take advantage of well-maintained gardens or landscaped yards that offer a peaceful retreat right outside your door.
  • Benefit from convenient parking options including driveways or designated parking spots near your accommodation.
  • Explore the outdoor space with a spacious balcony or deck, ideal for morning coffee or evening relaxation.
  • Make use of available recreational facilities such as basketball courts, tennis courts, or volleyball areas if provided.
  • Utilize outdoor grills or fire pits to enhance your experience and enjoy memorable cookouts in this destination.

Top Attractions Around Pleasant

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities and local attractions that showcase the area’s natural beauty and small-town charm, making it an ideal spot to explore during your stay.

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Family Activities

  • Pleasant Park: Enjoy a family picnic or a day of outdoor fun at this scenic park nestled within the region, perfect for relaxing with loved ones.
  • Museum of Local Heritage: Discover the area's rich history and culture through interactive exhibits that engage children and adults alike.
  • The Great Nature Trails: Embark on scenic hiking or biking adventures along well-maintained paths that showcase the natural beauty of this destination.
  • Community Water Playground: Splash around and beat the heat at this family-friendly water attraction, offering hours of entertainment for kids of all ages.
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Adult Activities

  • Golfing at Pleasant Valley Golf Course: Enjoy a relaxing day on the lush fairways, perfect for improving your swing in this scenic area.
  • Exploring local wineries and breweries: Sample regional wines and craft beers that showcase the region’s distinctive flavors and craftsmanship.
  • Visiting historic sites and museums: Discover the area's rich history through well-preserved landmarks and engaging exhibits.
  • Outdoor recreation at nearby parks: Take advantage of walking trails, picnicking spots, and scenic views in tranquil outdoor settings just outside your vacation rental.

Other Places to Stay in Pleasant, IL

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Pleasant Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Attractions: Take advantage of the regional calendar to discover nearby events and activities that enhance your stay without straying far from your vacation rental.
  • Plan Your Outdoor Adventures: Make the most of the area's natural beauty by scheduling outdoor excursions such as hiking, biking, or fishing around your comfortable vacation rental.
  • Utilize Local Dining Options: Experience authentic regional cuisine at local eateries, ensuring you indulge in the region's flavors while returning to your cozy accommodation.
  • Optimize Your Travel Timing: Consider visiting during off-peak seasons to enjoy fewer crowds and better rates at your preferred vacation rentals in this destination.

Transportation Options

  • Pleasant Transit Bus Service: This regional bus network offers convenient transportation options to explore the area and access nearby cities effortlessly.
  • Car Rentals at Pleasant Regional Airport: Renting a vehicle here provides flexibility and freedom to discover the region at your own pace.
  • Local Taxi Services in Pleasant, Illinois: Trusted taxi providers are available for quick, reliable rides within this destination and surrounding communities.
  • Shared Shuttle Services: Affordable shuttle options connect you to major transportation hubs and popular sites across the region, making travel seamless during your stay.

Local Customs Options

  • Southern Hospitality: Locals here take pride in their warm and welcoming attitude, making visitors feel like part of the community during your stay.
  • Family-Focused Celebrations: You might notice that family-oriented events and gatherings are a cornerstone of the region’s cultural calendar, reflecting its close-knit community values.
  • Traditional Local Cuisine: Embracing regional flavors, residents often gather for meals featuring hearty dishes that showcase the area's culinary heritage.
  • Community Festivals: Throughout the year, local festivals highlight the area's history and customs, offering authentic experiences to travelers seeking cultural connection.

Frequently Asked Questions About Pleasant?

1. What are the top vacation rentals in Pleasant?

There are a lot of options in Pleasant. If you plan on staying in the Pleasant area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pleasant:

2. Which vacation homes in Pleasant are best for families?

If you are looking for a family-friendly vacation home in Pleasant, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pleasant:

3. How many Rentbyowner vacation rentals are available in Pleasant?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 96 in the Pleasant 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 Pleasant.