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

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2118 Best Family Vacation Rentals in Assawoman Bay (Starting from $229)

309 White Heron Court
309 White Heron Court
House
Ocean City, MD, USA
1.9k from Assawoman Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

5 Bedrooms14 Guests
New to Booking
$1503
Average price / night
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Stunning 2BR/2BA Bayfront Retreat
Stunning 2BR/2BA Bayfront Retreat
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

2 Bedrooms7 Guests
9.6

Exceptional

14 reviews

$271
Average price / night
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5-6BR, 5BA in Bayside Retreat with Community Pools & Boat Slip
5-6BR, 5BA in Bayside Retreat with Community Pools & Boat Slip
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

6 Bedrooms18 Guests
10.0

Exceptional

198 reviews

$763
Average price / night
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Bayfront Condo with Amazing Views
Bayfront Condo with Amazing Views
House
Ocean City, MD, USA
2.0k from Assawoman Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$401
Average price / night
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Luxurious Bayfront Home,  OC MD On the water, Sleeps 12 guest,  Boat access.
Luxurious Bayfront Home, OC MD On the water, Sleeps 12 guest, Boat access.
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

3 Bedrooms12 Guests
10.0

Exceptional

86 reviews

$328
Average price / night
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Bayside Beauty
Bayside Beauty
Apartment
Ocean City, USA
2.0k from Assawoman Bay center

Apartments, Accommodations, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
8.0

Good

2 reviews

$638
Average price / night
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Escape to Elegance: Heron Harbor Condo, Your Bayside Retreat
Escape to Elegance: Heron Harbor Condo, Your Bayside Retreat
Condo
Ocean City, MD, 21842, United States
2.2k from Assawoman Bay center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$476
Average price / night
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Shipwreck Townhome
Shipwreck Townhome
House
Ocean City, MD, USA
2.0k from Assawoman Bay center

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

3 Bedrooms11 Guests
9.0

Fabulous

2 reviews

$620
Average price / night
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Bayfront, Sleeps 10, Boat Slip, 3 BR/2.5 BATH, Main Pool Open After Labor Day
Bayfront, Sleeps 10, Boat Slip, 3 BR/2.5 BATH, Main Pool Open After Labor Day
House
Ocean City, MD, 21842, United States
2.2k from Assawoman Bay center

AC, Balcony, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

18 reviews

$665
Average price / night
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Seaward Road #5 - Bay Bliss
Seaward Road #5 - Bay Bliss
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

3 Bedrooms6 Guests
New to Booking
$690
Average price / night
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Entire 1,300 sq ft, 2 bed/2 bath Condo w/Central AC,\nFull Size Washer/Dryer,Wifi
Entire 1,300 sq ft, 2 bed/2 bath Condo w/Central AC,\nFull Size Washer/Dryer,Wifi
Condo
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$229
Average price / night
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Harbour Bay 23 Ocean City
Harbour Bay 23 Ocean City
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

3 Bedrooms8 Guests
New to Booking
$256
Average price / night
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Paradise location - beautiful Waterfront SFH - Decks/Dock - beach around corner!
Paradise location - beautiful Waterfront SFH - Decks/Dock - beach around corner!
House
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

3 Bedrooms8 Guests
9.8

Exceptional

8 reviews

$588
Average price / night
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Heron's Retreat
Heron's Retreat
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

6 Bedrooms15 Guests
8.0

Good

1 reviews

$1427
Average price / night
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Luxe Family Home, Sleeps 10, Community Pool
Luxe Family Home, Sleeps 10, Community Pool
House
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

3 Bedrooms10 Guests
10.0

Exceptional

18 reviews

$645
Average price / night
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Point Lookout
Point Lookout
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

3 Bedrooms8 Guests
New to Booking
$568
Average price / night
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Bermuda B107 -the ideal location for the Family looking to have it ALL!
Bermuda B107 -the ideal location for the Family looking to have it ALL!
Condo
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

3 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$349
Average price / night
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Harbor Bay
Harbor Bay
House
Assawoman Bay, Maryland, USA
2.1k from Assawoman Bay center

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

4 Bedrooms11 Guests
7.3

Good

26 reviews

$281
Average price / night
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Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
House
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms11 Guests
10.0

Exceptional

25 reviews

$377
Average price / night
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A Bungalow
A Bungalow
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
9.2

Superb

7 reviews

$307
Average price / night
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Heron's Nest OC: Newly-renovated, kid friendly, bayside.
Heron's Nest OC: Newly-renovated, kid friendly, bayside.
Condo
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

2 Bedrooms5 Guests
10.0

Exceptional

7 reviews

$310
Average price / night
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Beautiful Bayfront Condo with Breathtaking Sunsets
Beautiful Bayfront Condo with Breathtaking Sunsets
Condo
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

3 Bedrooms7 Guests
10.0

Exceptional

34 reviews

$280
Average price / night
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★Pineapple Bay★ ~ Private Pier + Sunsets
★Pineapple Bay★ ~ Private Pier + Sunsets
House
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

AC, Arcade, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$546
Average price / night
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3 BR 2 BA Home in Montego Bay - Community Pool
3 BR 2 BA Home in Montego Bay - Community Pool
House
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

36 reviews

$394
Average price / night
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Quiet Family Condo in Hidden Harbour
Quiet Family Condo in Hidden Harbour
Condo
Ocean City, MD, 21842, United States
2.5k from Assawoman Bay center

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

2 Bedrooms7 Guests
10.0

Exceptional

13 reviews

$270
Average price / night
Check Availability
Pop Pop's Place in Montego Bay
Pop Pop's Place in Montego Bay
House
Ocean City, MD, 21842, United States
2.5k from Assawoman Bay center

AC, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Pool, Tennis Court

3 Bedrooms5 Guests
New to Booking
$397
Average price / night
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Harbor-View Balcony, Walk to Beach: Ocean City Gem
Harbor-View Balcony, Walk to Beach: Ocean City Gem
House
Ocean City, MD, 21842, United States
2.5k from Assawoman Bay center

AC, Balcony, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms8 Guests
9.6

Exceptional

26 reviews

$445
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 Assawoman Bay.

Where to stay in Assawoman Bay? Best neighborhoods & areas

Assawoman Bay Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2118 verified family-friendly vacation rentals in Assawoman Bay. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Assawoman Bay vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $229 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Assawoman 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 Assawoman 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 Assawoman Bay often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. 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.