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

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  5.  Assawoman Bay

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2865 Best Vacation Rentals with Pool in Assawoman Bay (Starting from $159)

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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★★★★★ 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
2.1k from Assawoman Bay center

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

1 Bedroom6 Guests
10.0

Exceptional

74 reviews

$255
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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Beautiful View of the Bay, 2 Bedroom Condo, Sleeps 6
Beautiful View of the Bay, 2 Bedroom Condo, Sleeps 6
Condo
Ocean City, MD, 21842, United States
2.1k from Assawoman Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

38 reviews

$359
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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First Floor 3BR/2BA Waterfront Condo w/ Pools! Discount and linens for 7 nights!
First Floor 3BR/2BA Waterfront Condo w/ Pools! Discount and linens for 7 nights!
Condo
Ocean City, MD, 21842, United States
2.2k from Assawoman Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$341
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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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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Harbour Bay 34 townhouse
Harbour Bay 34 townhouse
House
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

2 Bedrooms8 Guests
New to Booking
$159
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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Baywatch III 304D
Baywatch III 304D
Apartment
Ocean City, MD, USA
2.1k from Assawoman Bay center

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

3 Bedrooms6 Guests
New to Booking
$430
Average price / night
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North Ocean City - Montego Bay 3BR Home/ Beach, Pool, Pickleball and Mini Golf
North Ocean City - Montego Bay 3BR Home/ Beach, Pool, Pickleball and Mini Golf
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 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$268
Average price / night
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Harbor Sails 20301
Harbor Sails 20301
Apartment
Ocean City, MD, USA
2.2k from Assawoman Bay center

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

1 Bedroom4 Guests
7.9

Good

6 reviews

$252
Average price / night
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Beautiful - Newly renovated Bayfront - 3BR Townhome - Quiet, Pool, Boat Slip
Beautiful - Newly renovated Bayfront - 3BR Townhome - Quiet, Pool, Boat Slip
House
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

3 Bedrooms9 Guests
New to Booking
$658
Average price / night
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Heron Harbour 220-02
Heron Harbour 220-02
House
Ocean City, MD, USA
2.2k from Assawoman Bay center

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

3 Bedrooms10 Guests
New to Booking
$582
Average price / night
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Heron Harbour C103 by Seaside Vacations & Sales
Heron Harbour C103 by Seaside Vacations & Sales
Condo
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

4 Bedrooms9 Guests
New to Booking
$291
Average price / night
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Baywatch II 304D
Baywatch II 304D
Apartment
Ocean City, MD, USA
2.2k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$361
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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Harbor Sails 108
Harbor Sails 108
Apartment
Ocean City, MD, USA
2.2k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

1 Bedroom5 Guests
7.0

Good

1 reviews

$288
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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Baywatch II 303D
Baywatch II 303D
Apartment
Assawoman Bay, Maryland, USA
2.2k from Assawoman Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$272
Average price / night
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Nautical Lane 146 in popular Montego Bay
Nautical Lane 146 in popular Montego Bay
House
Ocean City, MD, 21842, United States
2.3k from Assawoman Bay center

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

4 Bedrooms10 Guests
9.6

Exceptional

11 reviews

$451
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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Cozy 2-bedroom condo with AC, WiFi in fantastic Ocean City
Cozy 2-bedroom condo with AC, WiFi in fantastic Ocean City
Condo
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

2 Bedrooms4 Guests
New to Booking
$360
Average price / night
Check Availability
Updated Condo in Popular Heron Harbour Community
Updated Condo in Popular Heron Harbour Community
Apartment
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

2 Bedrooms4 Guests
New to Booking
$308
Average price / night
Check Availability
Fabulous Condo Overlooking Canal w/Pool, Walking distance to Park/Beach
Fabulous Condo Overlooking Canal w/Pool, Walking distance to Park/Beach
Condo
Ocean City, MD, 21842, United States
2.4k from Assawoman Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$416
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
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 Pool in Assawoman Bay.

Where to stay in Assawoman Bay? Best neighborhoods & areas

Assawoman Bay Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2865 verified vacation rentals with a pool in Assawoman Bay. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Assawoman Bay vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $159 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Assawoman Bay offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Assawoman Bay welcome pets. Currently, 4 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Assawoman Bay often include additional outdoor features such as Pool, Laundry, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Assawoman Bay offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.