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- Rentals by Owner
Discover Your Ideal Caddy Shack Square Rental by Owner on Kelleys Island, Ohio for a Comfortable Stay
Discover Your Perfect Caddy Shack Square Rentals by Owner
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Rentals by Owner
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Caddy Shack Square Rentals by Owner
- Air Conditioner
- Parking
- Pool
- Parking
- View
- Accessibility
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Security/Safety
Why Choose Rent By Owner for your Caddy Shack Square vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Caddy Shack Square
When should you plan your Rentals by Owner stay?
Choosing the optimal time to visit ensures you can fully enjoy the local charm and relaxing atmosphere of the area, making your rental experience here both enjoyable and memorable.
Peak Season Highlights
Summer (June - August)
During the peak summer months, you will experience warm weather ideal for enjoying the outdoors and exploring this charming destination. Booking your rental here during this time ensures a vibrant atmosphere and lively community events.
Fall (September - October)
Early fall offers pleasant temperatures and beautiful foliage, making it a popular time for visitors seeking a peaceful retreat in this region. Securing your stay by owner now guarantees access to the area's scenic beauty and local festivities.
Off-Season Highlights
Winter (December - February)
The winter months bring cooler temperatures, providing a quieter experience for those looking to escape the crowds. Booking a rental here off-season offers a cozy and tranquil retreat amid the winter landscape.
Spring (March - May)
Springtime heralds renewal with milder weather and blooming scenery, though fewer visitors tend to visit during these months. Reservations by owner now allow you to enjoy the area's natural beauty before the summer rush begins.
Weekly Weather Forecast for Caddy Shack Square
How to Book Your Caddy Shack Square vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Caddy Shack Square
Common Rentals by Owner Amenities
What amenities can you expect?
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 access to spacious outdoor patios or decks for relaxing and entertaining.
- Benefit from private or shared outdoor grills perfect for cookouts with family and friends.
- Make the most of beautifully maintained gardens or landscaped yards surrounding your rental.
- Take advantage of nearby walking trails or nature paths available for outdoor exploration.
- Relax in outdoor seating areas designed for enjoying the scenic views of the region.
- Utilize outdoor parking spaces convenient for exploring the area at your own pace.
- Access to outdoor recreational equipment, such as kayaks or bicycles, to enhance your stay here.
Top Attractions Around Caddy Shack Square
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities and scenic explorations that showcase the charming character of this region, making it an ideal spot for both relaxation and adventure during your stay.

Family Activities
- Caddy Shack Golf Course: Enjoy a family-friendly round of golf at this scenic course, perfect for both beginners and experienced players looking to share a fun outdoor activity.
- Kelleys Island State Park: Explore the natural beauty of the area with a picnic, scenic walking trails, or a relaxing day by the water at this popular park destination.
- Rock Collecting and Beachcombing: Discover unique stones and shells along the shores, providing an educational and entertaining experience for children and adults alike.
- Local Winery Tours: Experience family-friendly wine tastings and learn about local viticulture in a welcoming environment on the island.
Adult Activities
- Wine Tasting Tours: Explore local wineries and enjoy tasting sessions that showcase the region’s renowned vineyards, making your visit here both relaxing and flavorful.
- Golfing at the Area Courses: Tee off at nearby golf courses designed for all skill levels, offering a perfect way to unwind amidst scenic views of the region's natural beauty.
- Boating and Fishing Experiences: Take advantage of the area's lakeside setting by renting a boat or casting a line to enjoy tranquil moments on the water during your stay.
- Cultural and Art Galleries: Discover local art and cultural exhibits that reflect the region’s rich history and vibrant community spirit, adding an enriching aspect to your trip.
Caddy Shack Square Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Research local events and natural attractions around Caddy Shack Square to make the most of your visit and choose accommodations close to these highlights.
- Book Your Rental Early: Secure your stay in this area by reserving your vacation rental well in advance to ensure you find the perfect home-away-from-home, especially during peak seasons.
- Explore Local Cuisine: Take advantage of nearby dining options to experience regional flavors that complement your relaxing getaway on the island.
- Utilize Convenient Transportation: Familiarize yourself with local transportation options or consider renting a bike or scooter for easy access to the scenic surroundings and hidden gems here.
Transportation Options
- Ferry Services: You can enjoy scenic crossings to and from the area, providing a relaxed and picturesque way to arrive at your rental on Kelleys Island.
- Local Taxis and Rideshares: Convenient for quick trips within the region, these options make exploring the island and nearby points of interest hassle-free.
- Bicycle Rentals: A popular eco-friendly choice that allows you to explore the area at your own pace while taking in the natural beauty surrounding your accommodation.
- Private Car Rentals: Ideal if you prefer flexibility, offering the convenience of having your own transportation during your stay in this destination.
Local Customs Options
- Respect for the Local Environment: You are encouraged to honor and preserve the natural beauty of this destination by practicing eco-friendly habits during your stay.
- Community Engagement: Participating in local events and supporting small businesses here fosters a sense of community and enriches your experience.
- Casual Hospitality: Visitors typically embrace a laid-back attitude, reflecting the area's friendly and welcoming culture.
- Preservation of Local Heritage: Respect for traditional customs and practices is highly valued, helping you connect authentically with the region’s history.
Frequently Asked Questions About Caddy Shack Square Rentals by Owner
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:
- Quarry Vista Kelleys Island, 3 Bedroom, Golf Cart, Hot Tub
- Brand new vacation home, built 2022! Great Location on Kelleys Island!
- Kelleys Island Luxury Lake Shack
- The Island Retreat on Kelleys Is
- Kelleys Island Modern Condo
- New Construction for 2023. Lake Home with Quarry Views.
- Walk to Lake: Kelleys Island Gem w/Deck!
- Screened in back porch is a haven!
- Summer Wind Lake House - Kelley's Island, OH
- Kelleys Island Luxury Home On Secluded Private Road
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 59 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 rentals in Caddy Shack Square on Rent By Owner?
4. How do I confirm availability and secure my booking through Rent By Owner in this area?
5. Are there any additional fees I should be aware of when booking a rental by owner here?
6. What amenities are included with rentals in Caddy Shack Square on Rent By Owner?
7. Who should I contact if I have questions about my stay or need assistance while on site?
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