Beach Home Rentals in Assawoman Bay, MD: Compare 10+ Sites & Save

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439 Beach Home Rentals in Assawoman Bay (Starting from $112)

Stunning 2BR/2BA Bayfront Retreat
Stunning 2BR/2BA Bayfront Retreat
House
Ocean City, MD, USA
2.0k from Assawoman Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$493
Average price / night
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Spacious 5 bedroom, waterfront home w/grill, firepit, full kitchen & shared pool
Spacious 5 bedroom, waterfront home w/grill, firepit, full kitchen & shared pool
House
Ocean City, MD, 21842, United States
1.9k from Assawoman Bay center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Kitchen, Laundry

5 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$592
Average price / night
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Sandyhill Sun
Sandyhill Sun
House
Ocean City, MD, USA
2.4k from Assawoman Bay center

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

3 Bedrooms6 Guests
6.0

Review score

2 reviews

$247
Average price / night
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2 Bedroom Bayside Condo with Pool in OCMD
2 Bedroom Bayside Condo with Pool in OCMD
Apartment
Ocean City, MD, USA
2.5k from Assawoman Bay center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$443
Average price / night
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⭐️Brand New High End Luxury Bayside Mansion Pool⭐️
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms20 Guests
9.6

Exceptional

15 reviews

$2078
Average price / night
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Remodeled Ocean City Getaway with Harbor Views!
Remodeled Ocean City Getaway with Harbor Views!
House
Ocean City, MD, USA
2.5k from Assawoman Bay center

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

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$457
Average price / night
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Beautiful 3 BR 3.5 BA Town House With Open Bay Views
Beautiful 3 BR 3.5 BA Town House With Open Bay Views
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

3 Bedrooms7 Guests
9.6

Exceptional

4 reviews

$426
Average price / night
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Pop Pop's Place
Pop Pop's Place
House
Ocean City, MD, USA
2.5k from Assawoman Bay center

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

3 Bedrooms7 Guests
9.5

Superb

15 reviews

$308
Average price / night
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Harbour Bay 3
Harbour Bay 3
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Breakfast Available, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

2 Bedrooms5 Guests
New to Booking
$249
Average price / night
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2BR Capri Oceanfront Condo, Indoor pool, Massage chair, Brand New bathrooms 2025, unbeatable views!
2BR Capri Oceanfront Condo, Indoor pool, Massage chair, Brand New bathrooms 2025, unbeatable views!
Apartment
Ocean City, MD, USA
2.6k from Assawoman Bay center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms5 Guests
New to Booking
$665
Average price / night
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Bayfront Beauty - Shipwreck 102
Bayfront Beauty - Shipwreck 102
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

2 Bedrooms4 Guests
New to Booking
$374
Average price / night
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Beautiful Beach Home
Beautiful Beach Home
Apartment
Ocean City, MD, USA
2.6k from Assawoman Bay center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms8 Guests
New to Booking
$258
Average price / night
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2BR 2BA Bayfront Condo- You'll Get Amazing Views & Breathtaking Sunsets Here!
2BR 2BA Bayfront Condo- You'll Get Amazing Views & Breathtaking Sunsets Here!
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

AC, Balcony, Dryer, Extra Bed, Heater, Kitchen, Laundry, Living Area, No Smoking

2 Bedrooms6 Guests
9.6

Exceptional

143 reviews

$239
Average price / night
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Ocean City, MD Waterfront Villa
Ocean City, MD Waterfront Villa
Apartment
Ocean City, MD, USA
2.6k from Assawoman Bay center

Internet, Guest Services, Sports/Activities, View, Oceanfront, Air Conditioner, Fireplace/Heating

1 Bedroom6 Guests
8.7

Fabulous

14 reviews

$112
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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Canal Beach Home With Your Own Arcade!
Canal Beach Home With Your Own Arcade!
House
Ocean City, MD, USA
2.6k from Assawoman Bay center

Guest Services, Fireplace/Heating, Ocean View, Balcony/Terrace, Parking, Air Conditioner, Security/Safety

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$565
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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1 Mi to Beach Bayside Townhome in Ocean City!
1 Mi to Beach Bayside Townhome in Ocean City!
House
Assawoman Bay, Maryland, USA
2.8k from Assawoman Bay center

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

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$412
Average price / night
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Bayside Lighthouse Retreat w/ Private Boat Slip on Canal - Sleeps 12
Bayside Lighthouse Retreat w/ Private Boat Slip on Canal - Sleeps 12
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

4 Bedrooms12 Guests
9.6

Exceptional

35 reviews

$509
Average price / night
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Carousel 2202
Carousel 2202
Apartment
Ocean City, MD, USA
2.9k from Assawoman Bay center

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

3 Bedrooms12 Guests
5.0

Review score

1 reviews

$1234
Average price / night
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Waterfront townhouse w/drivate dock, bay views, outdoor shower
Waterfront townhouse w/drivate dock, bay views, outdoor shower
House
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

3 Bedrooms11 Guests
8.4

Very Good

8 reviews

$449
Average price / night
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North Port-Direct Bay Front Condo iwith Spectacular Views!
North Port-Direct Bay Front Condo iwith Spectacular Views!
Condo
Ocean City, MD, 21842, United States
2.0k from Assawoman Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$718
Average price / night
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Watergate - 2 Bedroom, 3rd Floor Condo with Great VIews!
Watergate - 2 Bedroom, 3rd Floor Condo with Great VIews!
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
5.0

Review score

2 reviews

$278
Average price / night
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New for 2024 - 3 BR 2 BA Unit with Water Views and a Pool
New for 2024 - 3 BR 2 BA Unit with Water Views and a Pool
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

AC, Balcony, Dryer, Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$293
Average price / night
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Bayfront Condo with Stunning Sunset Views
Bayfront Condo with Stunning Sunset Views
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

2 Bedrooms8 Guests
New to Booking
$347
Average price / night
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Harbour Bay-Cozy Canal-Front Condo – Pool & Water Views
Harbour Bay-Cozy Canal-Front Condo – Pool & Water Views
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
New to Booking
$380
Average price / night
Check Availability
Harbour Bay 5
Harbour Bay 5
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

3 Bedrooms6 Guests
New to Booking
$305
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 Beach Rentals in Assawoman Bay.

Where to stay in Assawoman Bay? Best neighborhoods & areas

Assawoman Bay Beach Rentals on the Map

Frequently Asked Questions

You can explore 439 verified beach rentals in Assawoman Bay. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Assawoman Bay vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $112 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Assawoman Bay offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Assawoman Bay welcome pets. Currently, 5 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Assawoman Bay often include amenities designed for coastal living, such as Ocean View, View, and Oceanfront. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.