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

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  2. Vacation Rentals with Private Pool
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  5.  Assawoman Bay

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513 Best Vacation Rentals with Private Pool in Assawoman Bay (Starting from $154)

Club Ocean Villa II 104
Club Ocean Villa II 104
Apartment
Ocean City, MD, USA
2.5k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$218
Average price / night
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Favorite place at the beach - Our Place at the Beach!
Favorite place at the beach - Our Place at the Beach!
Condo
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

64 reviews

$330
Average price / night
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Walk to Beach Condo with Pool Access in Ocean City!
Walk to Beach Condo with Pool Access in Ocean City!
Apartment
Ocean City, MD, USA
2.5k from Assawoman Bay center

Guest Services, Fireplace/Heating, Parking, Security/Safety, Internet, Pool, View

1 Bedroom8 Guests
New to Booking
$219
Average price / night
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Sunsets, Peace & Quiet, Next to Northside Park, Over 60 5 Star Reviews!
Sunsets, Peace & Quiet, Next to Northside Park, Over 60 5 Star Reviews!
Condo
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

2 Bedrooms4 Guests
10.0

Exceptional

60 reviews

$262
Average price / night
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Club Ocean Villas Ii 88 Condo
Club Ocean Villas Ii 88 Condo
Apartment
Ocean City, MD, USA
2.5k from Assawoman Bay center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$157
Average price / night
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★★★★★ Sleeps 6✓ Linens &Towels✓ Free Parking✓ Sunset View✓ Smart TVs✓ Pool ✓
★★★★★ Sleeps 6✓ Linens &Towels✓ Free Parking✓ Sunset View✓ Smart TVs✓ Pool ✓
Condo
Ocean City, MD, 21842, United States
2.5k from Assawoman Bay center

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

1 Bedroom7 Guests
10.0

Exceptional

56 reviews

$263
Average price / night
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Club Ocean Villas II 182 condo
Club Ocean Villas II 182 condo
Apartment
Ocean City, MD, USA
2.5k from Assawoman Bay center

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

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$185
Average price / night
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BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Condo
Ocean City, MD, 21842, United States
2.6k from Assawoman Bay center

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

2 Bedrooms8 Guests
9.8

Exceptional

131 reviews

$230
Average price / night
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Club Ocean Villa 2 97
Club Ocean Villa 2 97
Apartment
Assawoman Bay, Maryland, USA
2.5k from Assawoman Bay center

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

2 Bedrooms7 Guests
7.7

Good

9 reviews

$432
Average price / night
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Beautiful Beach Home
Beautiful Beach Home
Condo
Ocean City, MD, 21842, United States
2.6k from Assawoman Bay center

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

2 Bedrooms8 Guests
8.6

Fabulous

39 reviews

$256
Average price / night
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Club Ocean Villa 2 144
Club Ocean Villa 2 144
Apartment
Assawoman Bay, Maryland, USA
2.5k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms6 Guests
4.0

Review score

5 reviews

$154
Average price / night
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2BR/2BA-GROUND FLOOR UNIT W/HOT TUB-LINEN PACKAGE INCLUDED@ CLUB OCEAN VILLAS II
2BR/2BA-GROUND FLOOR UNIT W/HOT TUB-LINEN PACKAGE INCLUDED@ CLUB OCEAN VILLAS II
Condo
Ocean City, MD, 21842, United States
2.6k from Assawoman Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.2

Superb

19 reviews

$286
Average price / night
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Club Ocean Villa 2 74
Club Ocean Villa 2 74
Apartment
Assawoman Bay, Maryland, USA
2.5k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms6 Guests
5.6

Review score

10 reviews

$175
Average price / night
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Hidden Harbour 2BR/2BA – Bayside Condo w/ Pool, Steps to Sand & Northside Park!
Hidden Harbour 2BR/2BA – Bayside Condo w/ Pool, Steps to Sand & Northside Park!
Condo
Ocean City, MD, 21842, United States
2.6k from Assawoman Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$230
Average price / night
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Club Ocean Villa 2 117
Club Ocean Villa 2 117
Apartment
2.5k from Assawoman Bay center

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

2 Bedrooms4 Guests
7.1

Good

8 reviews

$253
Average price / night
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Serene Canal front condo w/Balcony, WiFi, AC & community pool access
Serene Canal front condo w/Balcony, WiFi, AC & community pool access
Condo
Ocean City, MD, 21842, United States
2.7k from Assawoman Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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Club Ocean Villa 2 33
Club Ocean Villa 2 33
Apartment
Assawoman Bay, Maryland, USA
2.5k from Assawoman Bay center

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

2 Bedrooms6 Guests
9.4

Superb

7 reviews

$272
Average price / night
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HPN-Stunning 2 Bedroom Direct Ocean Front Condo
HPN-Stunning 2 Bedroom Direct Ocean Front Condo
Condo
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

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

2 Bedrooms6 Guests
New to Booking
$732
Average price / night
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Club Ocean Villa II 184B
Club Ocean Villa II 184B
Apartment
Ocean City, MD, USA
2.6k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms4 Guests
7.0

Good

2 reviews

$324
Average price / night
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Ocean City Escape, Waterfront,  Pool,  Dock, Beach, Walk to Restaurants
Ocean City Escape, Waterfront, Pool, Dock, Beach, Walk to Restaurants
House
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, No Smoking

3 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$392
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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Sea Watch 3 Bedroom 2 bath condo - resort-style living with indoor pool, private theater & more
Sea Watch 3 Bedroom 2 bath condo - resort-style living with indoor pool, private theater & more
Condo
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

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

3 Bedrooms6 Guests
New to Booking
$536
Average price / night
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Remodled, Beautiful Beachfront Penthouse with Pool - Perfect Location!
Remodled, Beautiful Beachfront Penthouse with Pool - Perfect Location!
Condo
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

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

2 Bedrooms8 Guests
8.2

Very Good

25 reviews

$491
Average price / night
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Beautiful Bay Views *  2 Kayaks To Explore The Bay * Private Dock For Boat!* NEW MASTER BATH in 2022
Beautiful Bay Views * 2 Kayaks To Explore The Bay * Private Dock For Boat!* NEW MASTER BATH in 2022
House
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

70 reviews

$619
Average price / night
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Carousel Oceanfront Condo-Beautiful Ocean & Bay Views with Private Balcony
Carousel Oceanfront Condo-Beautiful Ocean & Bay Views with Private Balcony
Condo
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms8 Guests
9.4

Superb

122 reviews

$401
Average price / night
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Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Condo
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

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

2 Bedrooms8 Guests
9.6

Exceptional

49 reviews

$789
Average price / night
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Ocean calling & country concert availability!
Ocean calling & country concert availability!
Condo
Ocean City, MD, 21842, United States
3.0k from Assawoman Bay center

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

1 Bedroom6 Guests
9.0

Fabulous

35 reviews

$204
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 Vacation Rentals with Private Pool in Assawoman Bay.

Where to stay in Assawoman Bay? Best neighborhoods & areas

Assawoman Bay Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 513 verified vacation rentals with a private pool in Assawoman Bay. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Assawoman Bay vary depending on the property size, location, and travel season. Rates typically start from around $154 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Assawoman Bay also welcome pets. Currently, 3 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Assawoman Bay often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Assawoman Bay include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.