Short-Term Rentals in Caddy Shack Square, OH: Compare 10+ Sites & Save

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208 Best Short-Term Rentals in Caddy Shack Square (Starting from $171)

On Island Time at Kelleys Island Condo!
On Island Time at Kelleys Island Condo!
House
Kelleys Island, OH, USA
0.2k from Caddy Shack Square center

Internet, Fireplace/Heating, Parking, Air Conditioner, Pool, Security/Safety, Child Friendly

2 Bedrooms6 Guests
New to Booking
$556
Average price / night
Check Availability
On Island Time at Kelleys! Downtown Area
On Island Time at Kelleys! Downtown Area
Condo
Kelleys Island, OH, 43438, United States
0.2k from Caddy Shack Square center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$557
Average price / night
Check Availability
New! Kelleys Island Condo
New! Kelleys Island Condo
House
Kelleys Island, OH, USA
0.2k from Caddy Shack Square center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
9.0

Fabulous

4 reviews

$642
Average price / night
Check Availability
New! Large 2 Bedroom Kelleys Island Condo
New! Large 2 Bedroom Kelleys Island Condo
Condo
Kelleys Island, OH, 43438, United States
0.2k from Caddy Shack Square center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
8.2

Very Good

10 reviews

$341
Average price / night
Check Availability
Beck Lake House
Beck Lake House
House
Kelleys Island, OH, USA
1.5k from Caddy Shack Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom10 Guests
New to Booking
$551
Average price / night
Check Availability
Quarry's Edge with pool - 2 Bdrms 2 Bths
Quarry's Edge with pool - 2 Bdrms 2 Bths
House
Kelleys Island, OH, 43438, United States
0.2k from Caddy Shack Square center

AC, Internet, No Smoking, Washer

2 Bedrooms6 Guests
New to Booking
$404
Average price / night
Check Availability
Walk to Lake Kelleys Island Gem with Deck!
Walk to Lake Kelleys Island Gem with Deck!
House
Kelleys Island, OH, USA
2.6k from Caddy Shack Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$425
Average price / night
Check Availability
Upper Deck-Downtown, Walk to Everything, Sleeps 10
Upper Deck-Downtown, Walk to Everything, Sleeps 10
House
Kelleys Island, OH, 43438, United States
0.2k from Caddy Shack Square center

AC, Barbecue, Internet, Microwave, No Smoking, Washer

3 Bedrooms10 Guests
New to Booking
$777
Average price / night
Check Availability
Spacious Lakeside Cottage - 2 Miles to Marblehead!
Spacious Lakeside Cottage - 2 Miles to Marblehead!
House
Lakeside, OH, USA
6.3k from Caddy Shack Square center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms12 Guests
7.5

Good

2 reviews

$244
Average price / night
Check Availability
Downtown Unique House w/2 Apartments-5bdrms/4bths
Downtown Unique House w/2 Apartments-5bdrms/4bths
House
Kelleys Island, OH, 43438, United States
0.2k from Caddy Shack Square center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking

5 Bedrooms16 Guests
New to Booking
$1263
Average price / night
Check Availability
Walk to Lake Historic Lakeside Marblehead Cottage
Walk to Lake Historic Lakeside Marblehead Cottage
House
Caddy Shack Square, Kelleys Island, Ohio, USA
6.6k from Caddy Shack Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

3 Bedrooms7 Guests
New to Booking
$267
Average price / night
Check Availability
Destination Downtown Condo w/ pool-2 Bdrms 2 Bths
Destination Downtown Condo w/ pool-2 Bdrms 2 Bths
House
Kelleys Island, OH, 43438, United States
0.2k from Caddy Shack Square center

AC, Barbecue, Internet, Microwave, No Smoking, Pool, Washer

2 Bedrooms6 Guests
New to Booking
$415
Average price / night
Check Availability
Little Ted's Cottages
Little Ted's Cottages
House
Marblehead, OH, USA
8.4k from Caddy Shack Square center

B&bs, Cheap, Accommodations, Pools, Parking, Guest houses, Homestays, Pet-friendly, Lodgings

31 Bedrooms38 Guests
8.5

Very Good

55 reviews

$171
Average price / night
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Island Away - 3 bedrooms/2 bathrooms
Island Away - 3 bedrooms/2 bathrooms
Condo
Kelleys Island, OH, 43438, United States
0.3k from Caddy Shack Square center

AC, Barbecue, Dryer, Free Parking, Internet, Microwave, No Smoking, Pool, Washer

3 Bedrooms8 Guests
New to Booking
$456
Average price / night
Check Availability
Lakeside Marblehead Home with Screened Patio!
Lakeside Marblehead Home with Screened Patio!
House
Mineyahta-on-the Bay, OH, USA
8.7k from Caddy Shack Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms9 Guests
New to Booking
$331
Average price / night
Check Availability
Newly renovated 2-bedroom condo with WiFi, AC in lovely Kelleys Island
Newly renovated 2-bedroom condo with WiFi, AC in lovely Kelleys Island
Condo
Kelleys Island, OH, 43438, United States
0.5k from Caddy Shack Square center

AC, Dryer, Free Parking, Heater, Internet, Laundry, No Smoking, Pool, TV

2 Bedrooms6 Guests
8.6

Fabulous

4 reviews

$339
Average price / night
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Furnished Screened Porch Baypoint Resort Home!
Furnished Screened Porch Baypoint Resort Home!
House
Marblehead, OH, USA
8.7k from Caddy Shack Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$327
Average price / night
Check Availability
Kelleys Island Modern Condo
Kelleys Island Modern Condo
Apartment
Kelleys Island, OH, 43438, United States
0.6k from Caddy Shack Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$378
Average price / night
Check Availability
 Charming cottage - New in 2024 with AC and Golf cart on peaceful Kelleys Island
Charming cottage - New in 2024 with AC and Golf cart on peaceful Kelleys Island
House
Kelleys Island, OH, 43438, United States
0.7k from Caddy Shack Square center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$447
Average price / night
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Home on the shore. 2 person Studio amazing view
Home on the shore. 2 person Studio amazing view
House
Kelleys Island, OH, 43438, United States
0.8k from Caddy Shack Square center

AC, Heater, Internet, No Smoking

1 Bedroom2 Guests
New to Booking
$356
Average price / night
Check Availability
\"Kelleys Island Escape\" is a short walk from downtown Kelleys Island & sleeps 6.
\"Kelleys Island Escape\" is a short walk from downtown Kelleys Island & sleeps 6.
House
Kelleys Island, OH, 43438, United States
0.8k from Caddy Shack Square center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

100 reviews

$311
Average price / night
Check Availability
Lake view apartment w/ amazing views & centrally located in the heart of Kelleys
Lake view apartment w/ amazing views & centrally located in the heart of Kelleys
Apartment
Kelleys Island, OH, 43438, United States
0.9k from Caddy Shack Square center

AC, Heater, Internet, No Smoking

1 Bedroom4 Guests
New to Booking
$249
Average price / night
Check Availability
Limestone Landing - Pool, firepit, covered patio, & more!
Limestone Landing - Pool, firepit, covered patio, & more!
House
Kelleys Island, OH, 43438, United States
0.9k from Caddy Shack Square center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
New to Booking
$567
Average price / night
Check Availability
Kelleys Island Walk To Downtown
Kelleys Island Walk To Downtown
House
Kelleys Island, OH, 43438, United States
1.0k from Caddy Shack Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
New to Booking
$532
Average price / night
Check Availability
Quarry Vista Kelleys Island, 3 Bedroom, Golf Cart, Hot Tub
Quarry Vista Kelleys Island, 3 Bedroom, Golf Cart, Hot Tub
House
Kelleys Island, OH, 43438, United States
1.0k from Caddy Shack Square center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

55 reviews

$503
Average price / night
Check Availability
Charming lake front apartment in the heart of Kelleys Island.
Charming lake front apartment in the heart of Kelleys Island.
Apartment
Kelleys Island, OH, 43438, United States
1.1k from Caddy Shack Square center

AC, Barbecue, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom4 Guests
New to Booking
$275
Average price / night
Check Availability
One room studio for the couple who wants a porch on Lake Erie and fire pit
One room studio for the couple who wants a porch on Lake Erie and fire pit
House
Kelleys Island, OH, 43438, United States
1.1k from Caddy Shack Square center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

1 Bedroom2 Guests
New to Booking
$356
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Caddy Shack Square.

Caddy Shack Square Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 208 verified short-term rentals in Caddy Shack Square, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Caddy Shack Square vary depending on location, property size, and travel dates. Rates typically start from around $171 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Caddy Shack Square include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Caddy Shack Square, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Caddy Shack Square often include amenities such as Fireplace/Heating, Kitchen, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Caddy Shack Square are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.