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

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41 Best Private Beach Vacation Rentals in Assawoman Bay (Starting from $155)

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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Golden Sands 2101
Golden Sands 2101
Apartment
Assawoman Bay, Maryland, USA
3.0k from Assawoman Bay center

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

3 Bedrooms8 Guests
8.3

Very Good

3 reviews

$635
Average price / night
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Family Friendly 16th floor 2BR Atlantis, Direct Oceanfront, Open Balcony,
Family Friendly 16th floor 2BR Atlantis, Direct Oceanfront, Open Balcony,
Apartment
Ocean City, MD, USA
3.1k from Assawoman Bay center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Self-catering

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$678
Average price / night
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Love Above the Waves -Best Ocean View and Heated Pool
Love Above the Waves -Best Ocean View and Heated Pool
Apartment
Ocean City, MD, USA
3.1k from Assawoman Bay center

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

1 Bedroom3 Guests
9.3

Superb

3 reviews

$204
Average price / night
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Golden Sands III
Golden Sands III
Apartment
Ocean City, MD, USA
3.1k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Beach, Places to stay, Family, Beach rentals

20 Bedrooms68 Guests
4.0

Review score

4 reviews

$155
Average price / night
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Golden Sands 817
Golden Sands 817
Apartment
Ocean City, MD, USA
3.1k from Assawoman Bay center

Apartments, Accommodations, Pools, Serviced apartments, Lodgings, Beach, Places to stay

2 Bedrooms6 Guests
New to Booking
$532
Average price / night
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Bayside Resort - 36370 Day Lilly Pkwy
Bayside Resort - 36370 Day Lilly Pkwy
House
Selbyville, DE, USA
4.0k from Assawoman Bay center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Hot tubs

4 Bedrooms12 Guests
New to Booking
$571
Average price / night
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Sunset Island - 34 Seaside
Sunset Island - 34 Seaside
House
Ocean City, MD, USA
4.0k from Assawoman Bay center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$789
Average price / night
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Sunset Island - 14 Shore Point
Sunset Island - 14 Shore Point
House
Ocean City, MD, USA
4.0k from Assawoman Bay center

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

6 Bedrooms12 Guests
New to Booking
$842
Average price / night
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Resort-Style Retreat with Beach Access in Ocean City
Resort-Style Retreat with Beach Access in Ocean City
House
Ocean City, MD, USA
4.1k from Assawoman Bay center

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

4 Bedrooms9 Guests
New to Booking
$593
Average price / night
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Sunset Island - 15 Canal Side Mews
Sunset Island - 15 Canal Side Mews
House
Ocean City, MD, USA
4.1k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$1046
Average price / night
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Sunset Island - 35 Seaside
Sunset Island - 35 Seaside
House
Ocean City, MD, USA
4.1k from Assawoman Bay center

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

5 Bedrooms12 Guests
9.0

Fabulous

1 reviews

$574
Average price / night
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Sunset Island - 17 Corner Store
Sunset Island - 17 Corner Store
House
Ocean City, MD, USA
4.2k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$755
Average price / night
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Sunset Island - 35 Fountain 4D
Sunset Island - 35 Fountain 4D
Apartment
Ocean City, MD, USA
4.2k from Assawoman Bay center

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

3 Bedrooms8 Guests
New to Booking
$698
Average price / night
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Sunset Island 5C
Sunset Island 5C
Apartment
Assawoman Bay, Maryland, USA
4.2k from Assawoman Bay center

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

3 Bedrooms8 Guests
8.3

Very Good

3 reviews

$407
Average price / night
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Sunset Island - 5 Beachside Mews
Sunset Island - 5 Beachside Mews
House
Ocean City, MD, USA
4.2k from Assawoman Bay center

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

6 Bedrooms12 Guests
New to Booking
$790
Average price / night
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Sunset Island - 35 Fountain 3E
Sunset Island - 35 Fountain 3E
Apartment
Assawoman Bay, Maryland, USA
4.2k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering, Accessible hotels

3 Bedrooms8 Guests
8.0

Good

1 reviews

$520
Average price / night
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Sunset Island - 31 Fountain
Sunset Island - 31 Fountain
House
Ocean City, MD, USA
4.2k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$511
Average price / night
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Sunset Island - 37 Fountain Dr W 3D
Sunset Island - 37 Fountain Dr W 3D
Apartment
Assawoman Bay, Maryland, USA
4.2k from Assawoman Bay center

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

3 Bedrooms8 Guests
New to Booking
$881
Average price / night
Check Availability
Sunset Island - 6 Sunset Island 4E
Sunset Island - 6 Sunset Island 4E
Apartment
Assawoman Bay, Maryland, USA
4.2k from Assawoman Bay center

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

3 Bedrooms8 Guests
New to Booking
$525
Average price / night
Check Availability
Sunset Island - 6 Hidden Cove 4C
Sunset Island - 6 Hidden Cove 4C
Apartment
Ocean City, USA
4.2k from Assawoman Bay center

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

3 Bedrooms8 Guests
New to Booking
$473
Average price / night
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Sunset Island - 37 Fountain 2D
Sunset Island - 37 Fountain 2D
Apartment
Ocean City, MD, USA
4.2k from Assawoman Bay center

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

3 Bedrooms6 Guests
New to Booking
$362
Average price / night
Check Availability
Sunset Island - 52 Island Edge
Sunset Island - 52 Island Edge
House
Ocean City, MD, USA
4.3k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$544
Average price / night
Check Availability
Sunset Island - 12 Beach Walk
Sunset Island - 12 Beach Walk
House
Assawoman Bay, Maryland, USA
4.3k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$936
Average price / night
Check Availability
Sunset Island - 59 Island Edge
Sunset Island - 59 Island Edge
House
Ocean City, MD, USA
4.3k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$1138
Average price / night
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Sunset Island - 15 Beach Walk
Sunset Island - 15 Beach Walk
House
Ocean City, MD, USA
4.3k from Assawoman Bay center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

5 Bedrooms12 Guests
New to Booking
$875
Average price / night
Check Availability
Sunset Island - 57 Island Edge
Sunset Island - 57 Island Edge
House
Ocean City, MD, USA
4.3k from Assawoman Bay center

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

5 Bedrooms12 Guests
New to Booking
$400
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 Private Beach Vacation Rentals in Assawoman Bay.

Where to stay in Assawoman Bay? Best neighborhoods & areas

Assawoman Bay Private Beach Vacation Rentals on the Map

Frequently Asked Questions

You can explore 41 verified private beach vacation rentals in Assawoman Bay. These include secluded coastal homes and estates that offer direct beach access with a higher level of privacy.

Prices for private beach rentals in Assawoman Bay vary depending on the property size, location, and level of beach access. Rates typically start from around $155 per night, with higher prices for larger homes or properties located on more exclusive stretches of coastline.

A private beach rental typically provides direct access to a stretch of sand that is limited to guests or nearby residents. Access levels can vary by location, so reviewing property details can help you understand how secluded the beach area is.

Yes, some private beach rentals in Assawoman Bay welcome pets. Currently, 3 listings allow pets, although policies may vary. It’s also important to check local beach regulations for any seasonal or area-specific restrictions.

Private beach properties are often limited in number and in high demand, so booking 90 to 150 days in advance is recommended for the best selection. Planning early increases your chances of securing a more secluded and desirable property.

Private beach rentals in Assawoman Bay often include amenities such as View, Security/Safety, and Private Beach. These features enhance comfort and allow guests to enjoy a more private and relaxing coastal stay.

Yes, there is a difference. "Oceanfront" means the property is located directly by the water, while "Private Beach" typically indicates that access to the beach area is restricted or less crowded. This distinction is important for travelers seeking a quieter and more exclusive beach experience.