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Owner Direct Vacation Rentals in Caddy Shack Square

The Best Owner Direct Vacation Rentals in Caddy Shack Square. Explore thousands of vacation home rentals, large cabins, and villas near Caddy Shack Square

New! Kelleys Island Condo From US $642
         

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8.8 (7 Reviews)
House
New! Kelleys Island Condo
  • Air Conditioner
  • Parking
  • Pool

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On Island Time at Kelleys! Downtown Area From US $793
         

10.0 (4 Reviews)
Condo
On Island Time at Kelleys! Downtown Area
  • Air Conditioner
  • Parking
  • Pool

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Kelleys Island Venture Resort From US $92
         

8.8 (51 Reviews)
Hotel
Kelleys Island Venture Resort
  • Air Conditioner
  • Parking
  • Pool

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On Island Time at Kelleys Island Condo! From US $556
         

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New
House
On Island Time at Kelleys Island Condo!
  • Air Conditioner
  • Parking
  • Pool

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Walk to Lake: Kelleys Island Gem w/Deck! From US $485
         

10.0 (4 Reviews)
House
Walk to Lake: Kelleys Island Gem w/Deck!
  • Air Conditioner
  • Parking
  • TV

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Walk to Lake Kelleys Island Gem with Deck! From US $426
         

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New
House
Walk to Lake Kelleys Island Gem with Deck!
  • Parking
  • View
  • Accessibility

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Kelleys Island Modern Condo From US $378
         

10.0 (3 Reviews)
Apartment
Kelleys Island Modern Condo
  • Air Conditioner
  • Parking
  • Pool

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Beck Lake House From US $551
         

New
House
Beck Lake House
  • Air Conditioner
  • Parking
  • Security/Safety

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Modern A-Frame + Backyard + Firepit + BBQ From US $379
         

10.0 (2 Reviews)
Cottage
Modern A-Frame + Backyard + Firepit + BBQ
  • Air Conditioner
  • Parking
  • Pet Friendly

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Kelleys Island Venture Resort From US $269
         

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7.4 (50 Reviews)
Hotel
Kelleys Island Venture Resort
  • Air Conditioner
  • Pool
  • View

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"Kelleys Island Escape" is a short walk from downtown Kelleys Island & sleeps 6. From US $298
         

9.8 (100 Reviews)
House
"Kelleys Island Escape" is a short walk from downtown Kelleys Island & sleeps 6.
  • Air Conditioner
  • Parking
  • TV

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Lakefront place for you From US $441
         

9.6 (22 Reviews)
House
Lakefront place for you
  • Air Conditioner
  • Parking
  • TV

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Chalet, "On the Rock" Kelleys Island Ohio From US $253
         

9.0 (2 Reviews)
Ski Chalet
Chalet, "On the Rock" Kelleys Island Ohio
  • Air Conditioner
  • Parking
  • Pet Friendly

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Newly renovated 2-bedroom condo with WiFi, AC in lovely Kelleys Island From US $353
         

8.6 (4 Reviews)
Condo
Newly renovated 2-bedroom condo with WiFi, AC in lovely Kelleys Island
  • Air Conditioner
  • Parking
  • Pool

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New! Large 2 Bedroom Kelleys Island Condo From US $304
         

8.2 (10 Reviews)
Condo
New! Large 2 Bedroom Kelleys Island Condo
  • Air Conditioner
  • Parking
  • Pool

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Simply Kelleys Resort -Lakeview Lower- Charming and renovated 2-bed apartment! From US $416
         

8.0 (1 Review)
Apartment
Simply Kelleys Resort -Lakeview Lower- Charming and renovated 2-bed apartment!
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Charming lake front apartment in the heart of Kelleys Island. From US $276
         

New
Apartment
Charming lake front apartment in the heart of Kelleys Island.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Simply Kelleys Resort -The Great Escape West- charming and renovated 2-bed! From US $529
         

New
Apartment
Simply Kelleys Resort -The Great Escape West- charming and renovated 2-bed!
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Home on the shore. 2 person Studio amazing view From US $357
         

New
House
Home on the shore. 2 person Studio amazing view
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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One room studio for the couple who wants a porch on Lake Erie and fire pit From US $357
         

New
House
One room studio for the couple who wants a porch on Lake Erie and fire pit
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lake view apartment w/amazing views & centrally located in the heart of Kelleys From US $249
         

New
Apartment
Lake view apartment w/amazing views & centrally located in the heart of Kelleys
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Marblehead Suite at Kelley's Island Venture Resort From US $334
         

10.0 (1 Review)
Hotel
Marblehead Suite at Kelley's Island Venture Resort
  • Air Conditioner
  • Parking
  • Pool

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Vineyard Suite at Kelley's Island Venture Resort From US $123
         

9.0 (4 Reviews)
Hotel
Vineyard Suite at Kelley's Island Venture Resort
  • Air Conditioner
  • Parking
  • Pool

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Glacier Suite at Kelley's Island Venture Resort From US $123
         

9.0 (2 Reviews)
Hotel
Glacier Suite at Kelley's Island Venture Resort
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Caddy Shack Square.

Weather in Caddy Shack Square

View the weather forecast for Caddy Shack Square before booking your Caddy Shack Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Caddy Shack Square, OH

Ownerdirect offers a large selection of top attractions around Caddy Shack Square. Research things to do on your vacation before you visit Caddy Shack Square.


Cedar Point African Safari Wildlife Park Castaway Bay Waterpark Sports Force Parks at Cedar Point Sports Center Marblehead Lighthouse Rain Water Park Complex Catawba Island State Park Lake Erie Sandusky Speedway Goofy Golf Ghostly Manor Thrill Center Sandusky Mall Monsoon Lagoon Water Park Firelands Regional Medical Center Merry-Go-Round Museum Skateworld Inscription Rock South Bass Island Lighthouse Perry's Victory and International Peace Memorial Maritime Museum of Sandusky