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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Oceanfront Rentals
  3.  USA

  4.  Maryland

  5.  Assawoman Bay

Refine your search

Price per night

Amenity Filter

Rating

3896 Best Oceanfront 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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
⭐️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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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 Oceanfront Rentals in Assawoman Bay.

Where to stay in Assawoman Bay? Best neighborhoods & areas

Assawoman Bay Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 3896 verified oceanfront rentals in Assawoman Bay. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Assawoman Bay vary depending on the property size, exact beachfront location, and season. Rates typically start from around $112 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Assawoman Bay offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Assawoman Bay welcome pets. Currently, 5 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Assawoman Bay often include features designed for a comfortable coastal stay, such as Ocean View, View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.