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Bloomington Luxury Rentals

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Bloomington Pet Friendly Vacation Rentals

9.8 (45 Reviews)
Cabin
Serenity Bluff Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Bloomington on PetFriendly.io

Why Choose Rent By Owner for your Bloomington 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 Bloomington

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as the region offers distinct charms throughout the year that suit various vacation preferences.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences its peak tourist season, making it ideal for outdoor activities and enjoying warm weather in the region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Fall (September to November)

Autumn brings vibrant foliage and mild temperatures, attracting visitors who seek scenic views and a peaceful atmosphere here.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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Winter (December to February)

Winters tend to be quieter in this area, offering a cozy ambiance and fewer crowds, perfect for those seeking tranquility and winter serenity.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 15°F
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Spring (March to May)

Early spring features cooler weather and less foot traffic, providing an excellent opportunity for exploring at a relaxed pace before the busy summer season begins.

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

Weekly Weather Forecast for Bloomington

How to Book Your Bloomington 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 Bloomington

More Top-Rated Vacation Rentals in Bloomington 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

  • You can enjoy access to spacious outdoor patios or decks perfect for relaxing and entertaining.
  • Many properties offer private or shared outdoor grilling areas for preparing delicious meals under the open sky.
  • Expect well-maintained yards or gardens where you can unwind amidst nature’s beauty.
  • Look for properties that feature a fire pit, ideal for cozy evenings with family and friends.
  • Options often include outdoor furniture such as loungers and dining sets designed for enjoying the fresh air.
  • You may find opportunities for outdoor recreation like hiking or biking trails nearby the rental.
  • Some rentals provide waterfront access or views, allowing you to enjoy the scenic landscapes of the region.

Top Attractions Around Bloomington

What attractions are nearby?

Explore the nearby outdoor activities and local attractions that make this destination in southern Wisconsin a perfect place to unwind and enjoy nature during your stay.

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Family Activities

  • Hiking at Trollway Park: Enjoy scenic trails and family-friendly outdoor activities within this peaceful park, perfect for exploring nature in the area.
  • Fishing at Bloomington Lake: Spend quality time together casting lines and relaxing by the tranquil waters of this local lake, a favorite spot for families visiting here.
  • Visiting the Bloomington Historical Museum: Discover the region’s rich history through engaging exhibits that offer educational fun for all ages in this welcoming community.
  • Exploring Nearby State Forests: Embark on adventures in the surrounding forests with opportunities for picnicking, wildlife observation, and outdoor recreation for your family.
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Adult Activities

  • Explore Wisconsin River Adventures: Embark on guided kayaking or canoeing trips to experience the scenic beauty of the region’s waterways firsthand.
  • Visit local breweries and wineries: Sample craft beers and regional wines in this destination’s renowned establishments, perfect for a relaxed adult outing.
  • Enjoy outdoor golf courses: Play a round at nearby championship golf courses that offer stunning views and challenging fairways suitable for all skill levels.
  • Discover area cultural events: Attend local art shows, live music performances, and seasonal festivals that highlight the vibrant community here.

Bloomington Travel Tips

How Can You Make the Most of Your Stay?

  • Discover local outdoor activities: Take advantage of the region's scenic parks and trails to explore and enjoy the natural beauty surrounding your vacation rental.
  • Visit seasonal events and festivals: Check the local calendar for events that celebrate the area's culture, providing a memorable experience during your stay.
  • Plan nearby dining experiences: Explore the regional cuisine by visiting local eateries to savor authentic flavors unique to here.
  • Choose well-located vacation rentals: Opt for accommodations close to key attractions and amenities to maximize your time and convenience during your visit.

Transportation Options

  • Bloomington Transit: This local bus service provides convenient transportation options around the area, making it easy to explore nearby attractions and amenities.
  • Rental Car Services: Several rental agencies operate here, offering flexible vehicle options for exploring the region at your own pace.
  • Taxi and Rideshare Services: Taxis and rideshare apps like Uber and Lyft are available for quick, reliable trips within the destination and surrounding areas.
  • Biking and Walking Paths: The region boasts dedicated biking and walking routes that allow you to enjoy the scenic surroundings at an leisurely pace.

Local Customs Options

  • Local Harvest Celebrations: Embrace the area's agricultural roots by participating in seasonal harvest festivals held throughout the region near Bloomington.
  • Community Gatherings: Engage with residents during neighborhood events that highlight traditional Wisconsin customs and foster a welcoming atmosphere.
  • Traditional Cuisine Etiquette: Enjoy local dishes while observing customary dining practices that emphasize communal sharing and family-style meals common here.
  • Sustainable Living Practices: Experience the community’s commitment to eco-friendly habits, including recycling initiatives and conservation efforts prevalent throughout this destination.

Frequently Asked Questions About Bloomington?

1. What are the top vacation rentals in Bloomington?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 60 in the Bloomington 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 Bloomington. 

4. What is the cancellation policy for booking a vacation rental in Bloomington, Wisconsin?

Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees.

5. How do I confirm availability and secure my reservation in Bloomington, Wisconsin?

Availability can be checked through the listing on the booking platform. Once you find your preferred dates, follow the booking process and communicate with the property owner if needed to finalize your reservation.

6. Are there any additional fees or deposits when staying at a vacation rental here?

Additional fees such as cleaning charges, security deposits, or service fees are typically detailed within each listing. Always verify these details before confirming your booking by reviewing the property listing or contacting the owner.

7. What amenities are usually included in rentals around this destination?

Properties often feature amenities like Wi-Fi, parking, kitchen facilities, and outdoor spaces. For specific amenities, consult the individual listing to ensure it meets your needs.

8. What should I know about check-in and check-out procedures in this region's vacation rentals?

Check-in and check-out times vary by property. Details are provided in each listing, but reaching out directly to the host can help clarify any special instructions to ensure a smooth arrival and departure.