Anna Vacation Rentals with Pools

Bed & Breakfast

Nanny's Place- Cozy Porchview Getaway B&B by Shawnee Hills Wine Trail and Parks

10.0

Exceptional

(3 Reviews)

2 Bedrooms 1 Bath 6 Guests 1500 ft²

R3,857/Night 7 Nights - R26,994

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Hotel

Hotel 7 Inn Anna

6.6

Good

(217 Reviews)

1 Bath

R1,541/Night 7 Nights - R10,778

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Wine Country Farmhouse Private Lake! kayaks Fire Pit! On The Wine Trail!

Highly Rated

Other

Wine Country Farmhouse Private Lake! kayaks Fire Pit! On The Wine Trail!

10.0

Exceptional

(163 Reviews)

5 Bedrooms 3 Baths 18 Guests 3000 ft²

R8,013/Night 7 Nights - R56,097

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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

(411 Reviews)

1 Bedroom 1 Bath 3 Guests 500 ft²

R2,294/Night 7 Nights - R16,051

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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

R1,978/Night 7 Nights - R13,843

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Bed & Breakfast

Davie School Inn

10.0

Exceptional

(48 Reviews)

1 Bedroom 1 Bath

R2,899/Night 7 Nights - R20,287

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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

(164 Reviews)

2 Bedrooms 1 Bath 4 Guests 900 ft²

R3,202/Night 7 Nights - R22,412

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Magical Victorian near hiking wine trail

Price Dropped

House

Magical Victorian near hiking wine trail

8.0

Excellent

(1 Review)

4 Bedrooms 3 Baths 8 Guests 2798.62 ft²

R4,378/Night 7 Nights - R30,652

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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

(147 Reviews)

2 Bedrooms 1 Bath 4 Guests 900 ft²

R3,202/Night 7 Nights - R22,412

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House

Cozy Anna Home Near Southern Illinois Attractions!

10.0

Exceptional

(16 Reviews)

2 Bedrooms 1 Bath 4 Guests 1000 ft²

R3,086/Night 7 Nights - R21,605

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Cabin

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

10.0

Exceptional

(12 Reviews)

2 Bedrooms 1 Bath 4 Guests 720 ft²

R3,262/Night 7 Nights - R22,824

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Charming 2-bedroom with AC, WiFi in lovely Jonesboro

Price Dropped

House

Charming 2-bedroom with AC, WiFi in lovely Jonesboro

10.0

Exceptional

(8 Reviews)

2 Bedrooms 1 Bath 6 Guests

R2,824/Night 7 Nights - R19,759

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More Top-Rated Vacation Rentals with Pools in Anna Area

Why Choose Rent By Owner for your Anna Vacation Rentals with Pools?

What makes our Vacation Rentals with Pools 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 Vacation Rentals with Pools stay?

Timing your vacation to enjoy the best weather and leisure activities in this destination can significantly enhance your stay, especially when searching for rentals with pools that offer comfort and relaxation during your visit to the region.

Peak Season Highlights

Summer (June to August)

During the summer months, you can enjoy warm weather ideal for relaxing by your rentals with pools and making the most of outdoor activities in this region.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F

Fall (September to November)

Early fall offers pleasant temperatures and fewer crowds, making it a perfect time to indulge in outdoor leisure while staying at your preferred rentals with pools.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 55°F to 60°F

Off-Season Highlights

Winter (December to February)

In winter, the cooler climate means more indoor relaxation, but you'll still find comfortable conditions for enjoying rentals with pools if heated amenities are available.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Spring (March to May)

Spring offers mild weather and fewer visitors, providing a peaceful setting to enjoy your stay with pools as the area awakens into warmer weather.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Anna

How to Book Your Anna Vacation Rentals with Pools

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals with pools. 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 Vacation Rentals with Pools in Anna Area

Common Vacation Rentals with Pools Amenities

What amenities can you expect?

Our Vacation Rentals with Pools 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 your outdoor lounging experience with a private or shared swimming pool.
Benefit from spacious patios or decks perfect for relaxing or entertaining under the sun.
Take advantage of outdoor dining areas to savor meals al fresco with scenic views.
Make the most of lush yard spaces or gardens ideal for outdoor activities and games.
Utilize built-in grilling stations or BBQ setups to enhance your cookouts during your stay.
Relax in cozy outdoor seating areas designed for socializing and unwinding after your adventures.
Explore nearby outdoor amenities such as walking trails or parks to enjoy this area's natural beauty.

Top Attractions Around Anna

What attractions are nearby?

Within the area, you can enjoy a variety of outdoor activities and local attractions that provide a perfect backdrop to your stay, all just a short drive from charming eateries and scenic parks, making it an ideal destination for those seeking relaxing rentals with pools in this region.

Family Activities

Anna Recreation Center Enjoy family-friendly activities and indoor swimming pools that allow you to beat the heat while staying active during your stay.
Bluff City Park Spend a relaxing day exploring scenic walking trails, playgrounds, and picnic areas perfect for outdoor fun with your loved ones.
Nearby Lake of Egypt Experience water-based adventures such as fishing, kayaking, or simply relaxing lakeside in this tranquil setting close to Anna.
Local Community Events Participate in seasonal festivals and outdoor events hosted here, offering entertainment and activities suitable for all ages.

Adult Activities

Visit the Shawnee National Forest: Explore scenic trails and enjoy the natural beauty of this expansive forest, perfect for outdoor adventures during your stay.
Experience local wineries and breweries: Discover regional flavors at nearby wineries and breweries, offering tastings and tours that showcase the area’s distinctive beverage scene.
Enjoy fishing and boating in Lake of Egypt: Spend relaxing days by the water engaging in fishing, boating, or simply unwinding along the shoreline of this popular lake.
Explore historic sites and local museums: Dive into the area's heritage by visiting museums and historic landmarks, enriching your understanding of the region's culture and history.

Other Places to Stay in Anna, IL

Union County

Explore 105 Properties

Stokes

Explore 94 Properties

Union County Hospital

Explore 39 Properties

Shawnee Community College

Explore 32 Properties

Anna City Park

Explore 30 Properties

More Places to Stay Near Anna

Anna Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead: Secure your ideal rentals with pools in advance to ensure availability during peak travel times in the area.
Explore Local Amenities: Take advantage of nearby recreational facilities and dine-in options to enhance your stay in this destination.
Maximize Pool Time: Schedule your pool sessions early in the day or late afternoon to enjoy quieter, more relaxing moments at your rental property.
Stay Connected: Keep an eye on local event calendars and seasonal activities to fully immerse yourself in everything this region has to offer.

Transportation Options

Car Rentals: Renting a car is a convenient way to explore the area at your own pace and access nearby attractions with ease.
Public Transit: Local bus services provide an affordable transportation option, connecting you to key points within the region.
Taxi Services & Rideshares: Taxis and rideshare apps like Uber or Lyft offer quick and reliable transportation for short trips around here.
Bike Rentals: Biking is a scenic and eco-friendly method to navigate the local streets and enjoy the area's natural beauty.

Local Customs Options

Local Festivals: Engaging in the area's community festivals offers an authentic glimpse into its traditions and local spirit.
Food Customs: Sampling regional dishes provides insight into the region's culinary heritage and hospitality.
Religious Traditions: Respect for local religious practices and celebrations highlights the area's cultural diversity and history.
Handcrafts and Artistry: Exploring handmade crafts showcases the artistic talents and long-standing customs of this destination.

Frequently Asked Questions About Anna Rentals with Pools

1. What are the top Rentals With Pools 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 Rentals With Pools in Anna:

2. How many Rentals With Pools are available in Anna?

Currently, the total number of properties listed by RBO in 2026 is over 3 in the Anna area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Anna. 

3. What is the cancellation policy for rentals with pools in Anna, Illinois?

The cancellation policy varies depending on the specific property listing. It is recommended to review the individual rental terms and conditions prior to booking or contact the property owner directly for detailed information.

4. Are there any additional fees associated with booking a rental with a pool in the area?

Additional fees such as cleaning charges, service fees, or pool maintenance fees may apply. These details are specified in each listing, so be sure to read the description carefully or reach out to the owner for clarification.

5. How do I find rentals with pools that meet my specific needs in this region?

You can filter your search based on amenities, including pools, and specify your preferences such as size, type, or location within the area. For personalized assistance, contacting the host directly can also help narrow down your options.

6. What should I know about the check-in and check-out procedures for these properties?

Check-in and check-out times vary by property and are detailed in each listing. Some rentals may offer flexible arrangements, but it’s best to confirm these details with the owner before completing your booking.

7. Are pets allowed at rentals with pools in the area?

Pet policies differ between properties; some owners accept pets while others do not. Be sure to review the pet policy listed on the property page or contact the owner directly to ensure your furry friends are welcome.