Vacation Rentals in Isle of Wight Bay, MD: Compare 10+ Sites & Save

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3475 Best Vacation Rentals in Isle of Wight Bay (Starting from $149)

Runaway Bay 810
Runaway Bay 810
House
Ocean City, MD, USA
1.6k from Isle of Wight Bay center

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

4 Bedrooms10 Guests
7.0

Good

1 reviews

$474
Average price / night
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Ocean City Bayside Townhouse
Ocean City Bayside Townhouse
House
Ocean City, MD, 21842, United States
1.7k from Isle of Wight Bay center

AC, Free Parking, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms10 Guests
8.0

Good

1 reviews

$370
Average price / night
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Runaway Bay 76
Runaway Bay 76
House
Ocean City, MD, USA
1.8k from Isle of Wight Bay center

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

3 Bedrooms10 Guests
6.8

Good

9 reviews

$149
Average price / night
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Remodeled Retreat | 4BR w/ Dock & Outdoor Shower
Remodeled Retreat | 4BR w/ Dock & Outdoor Shower
House
Ocean City, MD, 21842, United States
1.7k from Isle of Wight Bay center

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

4 Bedrooms10 Guests
New to Booking
$1492
Average price / night
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Crab Harbour 4
Crab Harbour 4
House
Ocean City, MD, USA
1.9k from Isle of Wight Bay center

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

3 Bedrooms8 Guests
New to Booking
$556
Average price / night
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Windjammer Beach House
Windjammer Beach House
Apartment
Ocean City, MD, 21842, United States
1.8k from Isle of Wight Bay center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$518
Average price / night
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Ocean High by Capital Vacations
Ocean High by Capital Vacations
Apartment
Isle of Wight Bay, Ocean City, Maryland, USA
1.9k from Isle of Wight Bay center

Air Conditioner, Parking, Private Pool, Ocean View, Hot Tub, Laundry, Pool

5 Bedrooms13 Guests
8.0

Good

69 reviews

$718
Average price / night
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Runaway Bay Retreat with Outdoor Pool
Runaway Bay Retreat with Outdoor Pool
House
Ocean City, MD, 21842, United States
1.8k from Isle of Wight Bay center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms10 Guests
New to Booking
$617
Average price / night
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Penguin Drive
Penguin Drive
Apartment
Isle of Wight Bay, Ocean City, Maryland, USA
1.9k from Isle of Wight Bay center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family, Accessible hotels

2 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$189
Average price / night
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Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more
Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more
Apartment
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking

New to Booking
$159
Average price / night
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Sunset Fishing Paradise 3b b Bay Front Townhome
Sunset Fishing Paradise 3b b Bay Front Townhome
House
Ocean City, MD, USA
1.9k from Isle of Wight Bay center

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

3 Bedrooms8 Guests
9.2

Superb

6 reviews

$335
Average price / night
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Penguin's Perch
Penguin's Perch
Apartment
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Pool, TV

2 Bedrooms8 Guests
2.0

Review score

1 reviews

$259
Average price / night
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Crab Cove Unit 2
Crab Cove Unit 2
Apartment
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom5 Guests
7.3

Good

3 reviews

$338
Average price / night
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Trident by Bayshore | 2BR Apartment
Trident by Bayshore | 2BR Apartment
Apartment
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms10 Guests
New to Booking
$225
Average price / night
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Thunder Island 43B
Thunder Island 43B
Apartment
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$223
Average price / night
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Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC
Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC
House
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Balcony, Extra Bed, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms8 Guests
4.0

Review score

5 reviews

$323
Average price / night
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Sea Jay Townhouse 616C
Sea Jay Townhouse 616C
House
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms8 Guests
9.5

Superb

2 reviews

$189
Average price / night
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Crab Harbour 4-Baywater 28th St, W/D, AC
Crab Harbour 4-Baywater 28th St, W/D, AC
House
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Balcony, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
5.2

Review score

9 reviews

$290
Average price / night
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Thunder Island 75B
Thunder Island 75B
House
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Sports/Activities, Air Conditioner, Pool, Internet, Security/Safety, View, Parking

1 Bedroom7 Guests
New to Booking
$250
Average price / night
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Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC
Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC
House
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Living Area

2 Bedrooms8 Guests
New to Booking
$258
Average price / night
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Bay Club Resort
Bay Club Resort
Apartment
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

33 Bedrooms176 Guests
8.5

Very Good

294 reviews

$428
Average price / night
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BAYFRONT TOWNHOUSE with PICTURESQUE VIEWS,  Mid-town, Ocean City, Maryland
BAYFRONT TOWNHOUSE with PICTURESQUE VIEWS, Mid-town, Ocean City, Maryland
House
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

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

4 Bedrooms12 Guests
10.0

Exceptional

27 reviews

$967
Average price / night
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Makai Sunset Cove all-season indoor pool
Makai Sunset Cove all-season indoor pool
Apartment
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$316
Average price / night
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Spacious 3 Bedroom 3 Bathroom Townhome, Pool, and 30 Ft. Pier
Spacious 3 Bedroom 3 Bathroom Townhome, Pool, and 30 Ft. Pier
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$369
Average price / night
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Beach cart, roof and back decks, fast internet, 6 beds
Beach cart, roof and back decks, fast internet, 6 beds
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$520
Average price / night
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Adorable 2-bedroom townhome with outdoor POOL in Ocean City
Adorable 2-bedroom townhome with outdoor POOL in Ocean City
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

2 Bedrooms8 Guests
New to Booking
$230
Average price / night
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Beautiful, upscale 3 bedroom townhouse with free WiFi, and impeccable style located right in the bay downtown and just three blocks to the beach!
Beautiful, upscale 3 bedroom townhouse with free WiFi, and impeccable style located right in the bay downtown and just three blocks to the beach!
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Fireplace, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
6.0

Review score

7 reviews

$407
Average price / night
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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 Vacation Rentals in Isle of Wight Bay.

Where to stay in Isle of Wight Bay? Best neighborhoods & areas

Isle of Wight Bay Vacation Rentals on the Map

Frequently Asked Questions

You can explore 3475 verified vacation rentals in Isle of Wight Bay. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Isle of Wight Bay vary depending on the season, property size, and location. Rates typically start from around $149 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Isle of Wight Bay include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Isle of Wight Bay welcome pets. Currently, 7 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Isle of Wight Bay often include amenities such as Fireplace/Heating, Laundry, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.