Discover Your Perfect Caddy Shack Square Vacation Homes

Best Vacation Homes in Caddy Shack Square

Why Choose Rent By Owner for your Caddy Shack Square 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 Caddy Shack Square

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this charming destination ensures you can enjoy its natural beauty and tranquility, making your stay in Caddy Shack Square more memorable and relaxing.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy warm weather and longer days, making it ideal for outdoor activities and exploring this scenic destination. Expect peak occupancy as travelers flock to the area for its vibrant summer atmosphere.

Average Temperature Daytime: around 80°F - Nighttime: around 65°F
autumn
Fall (September to November)

Autumn brings colorful foliage and pleasant temperatures, attracting visitors looking to experience the region’s natural beauty. Booking your vacation rentals early ensures availability during this popular season.

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

Off-Season Highlights

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Winter (December to February)

In winter, cooler weather and fewer tourists create a peaceful retreat for those seeking tranquility. Securing your accommodations in advance offers the best chances for a comfortable stay during this quieter time.

Average Temperature Daytime: around 35°F - Nighttime: around 20°F
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Early Spring (March to May)

As the landscape begins to bloom, early spring offers mild weather and fewer visitors. This period provides an excellent opportunity to explore the area with more flexibility and less competition for vacation rentals.

Average Temperature Daytime: around 55°F - Nighttime: around 40°F

Weekly Weather Forecast for Caddy Shack Square

How to Book Your Caddy Shack Square 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 Caddy Shack Square

More Top-Rated Vacation Rentals in Caddy Shack Square 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 seating areas perfect for relaxing and dining al fresco.
  • Take advantage of private or shared grilling stations to prepare meals outdoors.
  • Make the most of designated fire pits for cozy evenings under the stars.
  • Benefit from access to well-maintained walking trails suitable for exploring the area’s natural beauty.
  • Relax on spacious patios or decks that offer scenic views of the surrounding landscape.
  • Utilize outdoor recreational equipment like kayaks, paddleboards, or bicycles often available nearby.
  • Experience secure outdoor storage for sports gear and outdoor equipment, ensuring convenience during your stay.

Top Attractions Around Caddy Shack Square

What attractions are nearby?

While staying here, you'll find countless opportunities to enjoy outdoor activities and scenic views just moments from your accommodation on this island destination.

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Family Activities

  • Kelleys Island Lime Kiln State Park: Explore this historic park where your family can enjoy scenic views and learn about the island’s limestone heritage.
  • Kelleys Island Nature & Wildlife Preserve: Discover the native flora and fauna through easy walking trails that offer educational insights suited for all ages.
  • Beach Activities at Lake Erie: Relax and play along the sandy shores, perfect for swimming, picnicking, or building sandcastles in the local lake area.
  • Biking around the Island: Rent bikes to explore the charming countryside and scenic paths that showcase the natural beauty of this regional destination.
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Adult Activities

  • Kelleys Island Wine Tasting Tours: Explore local wineries and enjoy tasting sessions amidst scenic vineyard views, a perfect way to unwind in this charming area.
  • Golfing at the Kelleys Island Golf Course: Tee off on well-maintained greens while taking in panoramic views of the region's natural beauty for an engaging adult activity.
  • Kayaking and Paddleboarding: Discover the calm waters around the island with rentals available nearby, offering a serene way to connect with nature here.
  • Visit Local Breweries: Sample craft beers and learn about the brewing process at popular spots nestled within the area’s vibrant local scene.

Caddy Shack Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Savor the area's fresh, regional cuisine by trying out nearby restaurants and eateries during your stay.
  • Plan outdoor activities: Take advantage of the region's natural beauty by engaging in outdoor pursuits like hiking, boating, or relaxing by the waterfront.
  • Visit the local shops: Discover unique souvenirs and essentials at the area’s charming shops to enrich your vacation experience.
  • Make the most of your mornings: Wake early to enjoy peaceful moments and capture scenic views before the day gets busy in this beautiful destination.

Transportation Options

  • Car Rentals: In the area, renting a car offers the flexibility to explore Kelleys Island at your own pace, making it an ideal choice for travelers staying near Caddy Shack Square.
  • Bicycle Rentals: Biking around the region provides a scenic and eco-friendly way to enjoy the natural beauty of this destination's surroundings.
  • Taxi Services: Taxis are readily available for convenient transfers within the region, especially for quick trips to local attractions or ferry terminals.
  • Ferry Transportation: The ferry offers a picturesque and practical mode of transportation connecting the island with nearby points on the mainland, perfect for day trips or exploring from Caddy Shack Square.

Local Customs Options

  • Greeting Customs: Locals here often greet visitors with a friendly nod or wave, reflecting the warm hospitality that characterizes this destination.
  • Local Dining Etiquette: When enjoying meals in the region, it’s common to share dishes family-style, emphasizing community and togetherness.
  • Recreational Traditions: Participating in outdoor activities such as boating and fishing is deeply rooted in the area’s culture, making them popular pastimes for visitors.
  • Festive Celebrations: Seasonal festivals and events are celebrated with enthusiasm, providing an authentic glimpse into the local customs of this destination.

Frequently Asked Questions About Caddy Shack Square?

1. What are the top vacation rentals in Caddy Shack Square?

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

2. How many Rentbyowner vacation rentals are available in Caddy Shack Square?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 102 in the Caddy Shack Square 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 Caddy Shack Square. 

3. What is the cancellation policy for vacation rentals in Caddy Shack Square, Kelleys Island?

Cancellation policies vary by listing, so it’s best to review the specific property's terms before booking. Contact the property owner directly through the listing for detailed information regarding cancellations and potential fees.

4. How do I confirm availability for a vacation rental on Kelleys Island?

Availability details are listed on each property page. To secure your dates, proceed with the booking process or reach out to the property owner to verify current availability and ask any specific questions.

5. Are there any additional fees or deposits required when booking in this area?

Additional fees such as cleaning fees, security deposits, or service charges are typically specified in the listing. Review all charges carefully and contact the host if you need clarification about any costs involved.

6. What amenities can I expect in vacation rentals on Kelleys Island?

Amenities vary between properties, but many include features like full kitchens, outdoor spaces, Wi-Fi, and parking. Check the listing details for a comprehensive list of what’s included in each rental.

7. How do I communicate special requests or questions about my stay in this region?

Use the messaging feature on the listing platform to contact the property owner directly. They are the best resource for addressing your specific needs or questions about the property and surrounding area.

Best Vacation Homes in Caddy Shack Square