Anna Rentals By Owner

Rest, Relax and Renew. Our log cabin experience awaits your arrival.

Highly Rated

Cabin

Rest, Relax and Renew. Our log cabin experience awaits your arrival.

10.0

Exceptional

(417 Reviews)

1 Bedroom 1 Bath 3 Guests 500 ft²

R3,268/Night 7 Nights - R22,876

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Cozy Anna Home Near Southern Illinois Attractions!

House

Cozy Anna Home Near Southern Illinois Attractions!

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 4 Guests 1001.04 ft²

R3,340/Night 7 Nights - R23,382

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Highly Rated

Cabin

Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery

10.0

Exceptional

(170 Reviews)

2 Bedrooms 1 Bath 4 Guests 900 ft²

R3,467/Night 7 Nights - R24,263

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House

Magical Victorian near hiking wine trail

8.0

Excellent

(1 Review)

4 Bedrooms 3 Baths 8 Guests 2798.62 ft²

R4,335/Night 7 Nights - R30,349

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New cabin in the woods with private hot tub

Highly Rated

Cabin

New cabin in the woods with private hot tub

10.0

Exceptional

(156 Reviews)

2 Bedrooms 1 Bath 4 Guests 900 ft²

R3,467/Night 7 Nights - R24,263

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House

Cozy Anna Home Near Southern Illinois Attractions!

10.0

Exceptional

(17 Reviews)

2 Bedrooms 1 Bath 4 Guests 1000 ft²

R3,109/Night 7 Nights - R21,767

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Cabin

Shawnee National Forest Romantic Lake Cabin with Hot Tub, near Wine Trail

10.0

Exceptional

(16 Reviews)

2 Bedrooms 1 Bath 4 Guests 720 ft²

R3,229/Night 7 Nights - R22,599

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House

Cozy and Updated Farmhouse with King Suite

10.0

Exceptional

(15 Reviews)

2 Bedrooms 2 Baths 6 Guests 950 ft²

R1,885/Night 7 Nights - R13,200

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Pa’s House is an enjoyable, entirely remodeled, 2-bedroom farmhouse near Anna.

Price Dropped

House

Pa’s House is an enjoyable, entirely remodeled, 2-bedroom farmhouse near Anna.

10.0

Exceptional

(4 Reviews)

2 Bedrooms 2 Baths 6 Guests

R4,778/Night 7 Nights - R33,450

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Spacious 2 BR, 1 1/2 baths, hot tub, pool table, outside room, full kitchen

Highly Rated

House

Spacious 2 BR, 1 1/2 baths, hot tub, pool table, outside room, full kitchen

9.8

Exceptional

(176 Reviews)

2 Bedrooms 1 Bath 6 Guests

R3,070/Night 7 Nights - R21,489

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Cabin

Shawnee Wine Trail Cabin on Lake, near Shawnee National Forest with Hot Tub.

9.8

Exceptional

(19 Reviews)

2 Bedrooms 1 Bath 4 Guests 720 ft²

R3,278/Night 7 Nights - R22,942

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Cabin

Tiny Cabin in the woods with perfect Sunsets

1 Bedroom 1 Bath 4 Guests

R2,179/Night 7 Nights - R15,256

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More Top-Rated Rentals by Owner in Anna Area

Why Choose Rent By Owner for your Anna vacation rental?

What makes our Rentals by Owner 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 Anna

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, whether you're seeking peaceful off-peak seasons or lively periods when local events take place in Anna, Illinois, USA.

Peak Season Highlights

Summer (June to August)

During the summer months, the area experiences its peak due to warm weather and longer days, making it ideal for exploring outdoor activities and enjoying local events.

Average Temperature Daytime: 85°F - Nighttime: 65°F

Fall (September to November)

Autumn brings vibrant foliage and cooler temperatures, attracting visitors seeking scenic drives and outdoor excursions in this region.

Average Temperature Daytime: 75°F - Nighttime: 50°F

Off-Season Highlights

Winter (December to February)

The winter season sees fewer visitors as temperatures drop, but it offers a peaceful environment for those who enjoy a quiet getaway.

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

Early Spring (March to April)

Early spring can be less crowded, with nature beginning to awaken, providing a serene setting for visitors willing to embrace transitional weather.

Average Temperature Daytime: 55°F - Nighttime: 35°F

Weekly Weather Forecast for Anna

How to Book Your Anna 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

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Anna

More Top-Rated Rentals by Owner in Anna 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 dining with a private barbecue grill area, perfect for gatherings in the region's pleasant weather.
Take advantage of a spacious backyard or garden space to relax or play games amidst nature.
Look for properties that offer a scenic patio or veranda, ideal for morning coffee or evening unwinding.
Experience the convenience of an outdoor fire pit for cozy evenings under the stars.
Seek out rentals with access to nearby hiking or walking trails to explore the local landscape.
Benefit from outdoor swimming pools available at some vacation homes in this area during warmer months.
Find accommodations featuring a private balcony or deck to enjoy panoramic views of the surrounding countryside.

Top Attractions Around Anna

What attractions are nearby?

While staying here, you can enjoy nearby outdoor activities, local parks, and cultural attractions that showcase the charm of this region, making your visit both relaxing and engaging.

Family Activities

Anna Area Parks and Recreation: Enjoy outdoor adventures with family-friendly parks offering playgrounds, walking trails, and open spaces perfect for picnics and leisure activities.
Museum of Local History: Explore the region’s heritage through engaging exhibits that provide educational fun for children and adults alike.
Community Events and Festivals: Participate in seasonal festivals and lively community gatherings that showcase the local culture and entertainment options for families.
Nearby Nature Trails: Discover scenic hiking and biking paths nearby where your family can connect with the natural beauty of this destination's surroundings.

Adult Activities

Visit the Anna-Jonesboro Country Club: Enjoy a round of golf or relax at this local club known for its scenic course and friendly atmosphere.
Explore nearby Lake Kruta: Engage in fishing, kayaking, or simply unwind by the water while experiencing the tranquil scenery of the region.
Experience local dining options: Savor regional specialities and authentic Southern Illinois cuisine at the area's popular restaurants.
Discover historic sites and landmarks: Take a leisurely tour of the area’s historical attractions that offer insight into the local heritage and culture.

Other Places to Stay in Anna, IL

Anna Travel Tips

How Can You Make the Most of Your Stay?

Explore local dining options: Take advantage of the region’s unique restaurants to enjoy authentic flavors during your stay.
Plan outdoor activities: Make the most of nearby parks and recreational areas for outdoor adventures that showcase the area's natural beauty.
Check for seasonal events: Align your visit with local festivals or community events to immerse yourself in the local culture.
Utilize local tips and recommendations: Connect with your rental host for insights on hidden gems and must-see spots around this destination.

Transportation Options

Regional Airport: You can access the area conveniently via the nearby regional airport, offering scheduled flights and quick connectivity.
Taxi and Rideshare Services: Reliable taxi and rideshare options are available for comfortable travel within this part of Illinois.
Car Rentals: Renting a car is a practical way to explore the region at your own pace, with numerous agencies serving this destination.
Public Transit: Local bus services provide an economical transportation alternative for getting around here and reaching surrounding areas.

Local Customs Options

Respect for Local Agriculture: You will notice that embracing the area's farming traditions is appreciated when visiting or staying here, reflecting the community’s agricultural roots.
Community Events and Gatherings: Participating in local festivals and events is a valued tradition that helps you connect with residents and experience the region's vibrant culture.
Honoring Historical Heritage: Recognizing and respecting the historical landmarks and sites highlights your appreciation for the area's rich history and preserves its unique identity.
Courteous Interaction: Engaging politely with neighbors and locals through friendly conversations embodies the welcoming spirit typical of this region’s customs.

Frequently Asked Questions About Anna Rentals by Owner

1. What are the top Vacation Rentals in Anna?

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

2. How many Vacation Rentals are available in Anna?

Currently, the total number of properties listed by RBO in 2026 is over 26 in the Anna area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Anna. 

3. What is the cancellation policy when booking a rental by owner in the Anna area?

Cancellation policies vary by listing. To find specific details about your reservation, please review the terms outlined on the listing page or contact the property owner directly.

4. How can I communicate with the property owner before booking my rental in this region?

You can reach out to the owner through the messaging platform provided on the booking site to ask questions or clarify details about the rental before confirming your reservation.

5. Are there any additional fees I should be aware of for rentals in Anna, Illinois?

Additional fees such as cleaning, service charges, or taxes are listed in the booking details. Be sure to review the total cost before finalizing your reservation.

6. What amenities are typically included in private rentals here?

Amenities vary by property, but common features include Wi-Fi, parking, kitchen facilities, and laundry options. Check each listing for a detailed list of available amenities.

7. How do I ensure my stay complies with local regulations when booking a rental by owner in this area?

It's recommended to review all house rules and local regulations specified by the owner on the listing. If you have concerns, contact the owner directly to clarify any compliance requirements.