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

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2137 Best Family 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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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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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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Bayside Townhome Close to Beach and Boardwalk!
Bayside Townhome Close to Beach and Boardwalk!
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

31 reviews

$308
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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Walk to Beach! Family-Friendly Ocean City Condo
Walk to Beach! Family-Friendly Ocean City Condo
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

AC, Balcony, Crib, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms8 Guests
9.8

Exceptional

10 reviews

$493
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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Bright Townhome on the Bay with Pool, Short Walk to Beach and Boardwalk
Bright Townhome on the Bay with Pool, Short Walk to Beach and Boardwalk
House
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$376
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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XPLORIE ACTIVITIES & LINENS INCLUDED*!  PANORAMIC VIEWS!! Bahama Princess-Direct bayfront 2BR/2BA condo.
XPLORIE ACTIVITIES & LINENS INCLUDED*! PANORAMIC VIEWS!! Bahama Princess-Direct bayfront 2BR/2BA condo.
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

AC, Balcony, Dryer, Extra Bed, Kitchen, Laundry, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
8.8

Fabulous

8 reviews

$172
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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Bayfront, fully refinished, stunning views, spacious Condo, steps from the beach
Bayfront, fully refinished, stunning views, spacious Condo, steps from the beach
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
9.8

Exceptional

64 reviews

$371
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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DownByTheBay_4601-  Spacious Penthouse home next to Seacrets & Convention Center
DownByTheBay_4601- Spacious Penthouse home next to Seacrets & Convention Center
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet

4 Bedrooms15 Guests
9.6

Exceptional

21 reviews

$361
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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Bayside Pearl @ Thunder Island 170D.  2 Bed 2 Bath, Pool, Marina, Sleeps 8
Bayside Pearl @ Thunder Island 170D. 2 Bed 2 Bath, Pool, Marina, Sleeps 8
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$277
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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Everything imaginable! In & outdoor pools, ocean and bay views, a huge patio.
Everything imaginable! In & outdoor pools, ocean and bay views, a huge patio.
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub

3 Bedrooms10 Guests
9.6

Exceptional

112 reviews

$402
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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Canal - Waterfront, WIFI, Walking Distance to Boardwalk / Beach, Bring Your Boat
Canal - Waterfront, WIFI, Walking Distance to Boardwalk / Beach, Bring Your Boat
House
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

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

3 Bedrooms7 Guests
9.0

Fabulous

30 reviews

$367
Average price / night
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Walk to Pool & Beach! Family Condo in Ocean City
Walk to Pool & Beach! Family Condo in Ocean City
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

AC, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.4

Very Good

5 reviews

$344
Average price / night
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1 Mi to Jolly Roger! Poolside Family Retreat
1 Mi to Jolly Roger! Poolside Family Retreat
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$292
Average price / night
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Great location, Great condo, WOW about this place!  Book your 2025 dates now!
Great location, Great condo, WOW about this place! Book your 2025 dates now!
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Crib, Dryer, Elevator, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

44 reviews

$336
Average price / night
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Stroll to Shore! Condo w/ Balcony in Ocean City
Stroll to Shore! Condo w/ Balcony in Ocean City
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

51 reviews

$469
Average price / night
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Perfect Bay, Beach and Pool Condo for a Family!
Perfect Bay, Beach and Pool Condo for a Family!
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

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

1 Bedroom5 Guests
9.8

Exceptional

48 reviews

$231
Average price / night
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Located across from the Convention Center and steps to the beach! 5 Star Rating!
Located across from the Convention Center and steps to the beach! 5 Star Rating!
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms10 Guests
10.0

Exceptional

68 reviews

$357
Average price / night
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Luxury Condo - Ocean view!  spacious 1,728 sq ft. Sun. to Sun. rentals in summer
Luxury Condo - Ocean view! spacious 1,728 sq ft. Sun. to Sun. rentals in summer
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms10 Guests
10.0

Exceptional

95 reviews

$470
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 Family Vacation Rentals in Isle of Wight Bay.

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

Isle of Wight Bay Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2137 verified family-friendly vacation rentals in Isle of Wight Bay. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Isle of Wight Bay vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $149 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Isle of Wight Bay offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Isle of Wight Bay are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Isle of Wight Bay often include amenities such as Child Friendly, Laundry, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.