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

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  2. Vacation Rentals with Private Pool
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  5.  Isle of Wight Bay

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509 Best Vacation Rentals with Private Pool in Isle of Wight Bay (Starting from $141)

Ocean High by Capital Vacations
Ocean High by Capital Vacations
Apartment
Isle of Wight Bay, Ocean City, Maryland, USA
1.9k from Isle of Wight Bay center

Air Conditioner, Parking, Private Pool, Ocean View, Hot Tub, Laundry, Pool

5 Bedrooms13 Guests
8.0

Good

69 reviews

$718
Average price / night
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Gorgeous Views, Direct Bayfront Condo
Gorgeous Views, Direct Bayfront Condo
Condo
Ocean City, MD, 21842, United States
1.8k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
9.8

Exceptional

51 reviews

$250
Average price / night
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Bay Club Resort
Bay Club Resort
Apartment
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

33 Bedrooms176 Guests
8.5

Very Good

294 reviews

$428
Average price / night
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2 bedroom condo Located on 28th street
2 bedroom condo Located on 28th street
Condo
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
New to Booking
$339
Average price / night
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Bay Front Paradise Penthouse Unit
Bay Front Paradise Penthouse Unit
Apartment
Ocean City, MD, USA
2.1k from Isle of Wight Bay center

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

3 Bedrooms8 Guests
9.7

Exceptional

3 reviews

$855
Average price / night
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Walk to Beach! Family-Friendly Ocean City Condo
Walk to Beach! Family-Friendly Ocean City Condo
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

AC, Balcony, Crib, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms8 Guests
9.8

Exceptional

10 reviews

$493
Average price / night
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Future One 2
Future One 2
Apartment
Ocean City, MD, USA
2.2k from Isle of Wight Bay center

Apartments, Accommodations, Pools, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$141
Average price / night
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Gorgeous Remodel Wight Bay 2BD 2BA Waterfront-Near Convention Center & Seacrets
Gorgeous Remodel Wight Bay 2BD 2BA Waterfront-Near Convention Center & Seacrets
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
9.6

Exceptional

54 reviews

$359
Average price / night
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Bella Vista 505
Bella Vista 505
Apartment
Ocean City, MD, USA
2.2k from Isle of Wight Bay center

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

1 Bedroom8 Guests
New to Booking
$304
Average price / night
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Cozy Loft Style Condo Overlooking Canal
Cozy Loft Style Condo Overlooking Canal
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$366
Average price / night
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Makai 613
Makai 613
Apartment
Ocean City, MD, USA
2.2k from Isle of Wight Bay center

Internet, Fireplace/Heating, Air Conditioner, Pool, Security/Safety, View, Private Pool

1 Bedroom6 Guests
New to Booking
$253
Average price / night
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\"A Shore Thing\" is Family friendly \nOcean City MD\nWalking distance to The beach!
\"A Shore Thing\" is Family friendly \nOcean City MD\nWalking distance to The beach!
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

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

2 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$339
Average price / night
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Ocean City Vacation Homes Property Luxurious Bayfront Condo
Ocean City Vacation Homes Property Luxurious Bayfront Condo
Apartment
Ocean City, MD, USA
2.2k from Isle of Wight Bay center

Sports/Activities, Air Conditioner, Accessibility, Security/Safety, Pool, Internet, Private Pool

1 Bedroom8 Guests
New to Booking
$381
Average price / night
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MAKAI'S CONVENTION CENTER NEWLY REMODELED OC INDOOR POOL FITNESS BILLIARDS
MAKAI'S CONVENTION CENTER NEWLY REMODELED OC INDOOR POOL FITNESS BILLIARDS
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

AC, Arcade, Balcony, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
9.4

Superb

179 reviews

$213
Average price / night
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Makai 108
Makai 108
Apartment
Ocean City, MD, USA
2.2k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
7.3

Good

14 reviews

$179
Average price / night
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Wight Bay - 2BR/2BA Direct Bay Front - Stunning Bay View!
Wight Bay - 2BR/2BA Direct Bay Front - Stunning Bay View!
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
9.4

Superb

56 reviews

$227
Average price / night
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Gateway Grand
Gateway Grand
Apartment
Ocean City, MD, USA
2.3k from Isle of Wight Bay center

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

6 Bedrooms19 Guests
6.3

Good

3 reviews

$414
Average price / night
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 Makai - Luxury Bayfront Condo - 4th Floor - Amazing Water Views
Makai - Luxury Bayfront Condo - 4th Floor - Amazing Water Views
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
9.8

Exceptional

99 reviews

$464
Average price / night
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Gateway Grand 301
Gateway Grand 301
Apartment
Isle of Wight Bay, Ocean City, Maryland, USA
2.4k from Isle of Wight Bay center

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

4 Bedrooms10 Guests
New to Booking
$866
Average price / night
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Thunder Island \"A\" Building,  Gorgeous Direct Bay Front, Close to Beach
Thunder Island \"A\" Building, Gorgeous Direct Bay Front, Close to Beach
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

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

2 Bedrooms7 Guests
10.0

Exceptional

78 reviews

$303
Average price / night
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Magnificent Bay View!!! Luxurious Condo, Your Home-Away-From-Home, Makai #316
Magnificent Bay View!!! Luxurious Condo, Your Home-Away-From-Home, Makai #316
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

AC, Arcade, Balcony, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms7 Guests
10.0

Exceptional

68 reviews

$353
Average price / night
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Walk to Pool & Beach! Family Condo in Ocean City
Walk to Pool & Beach! Family Condo in Ocean City
Condo
Ocean City, MD, 21842, United States
2.2k from Isle of Wight Bay center

AC, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.4

Very Good

5 reviews

$344
Average price / night
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Luxury Waterfront Oasis with Pool & Beach Access
Luxury Waterfront Oasis with Pool & Beach Access
House
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

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

4 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$646
Average price / night
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Brand new smart TV's in every bedroom  -  Brand New 55 inch TV in Living Room
Brand new smart TV's in every bedroom - Brand New 55 inch TV in Living Room
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
9.8

Exceptional

41 reviews

$488
Average price / night
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Bright & Beautiful Bay View Condo Overlooking Pool in Great Mid-Town Location
Bright & Beautiful Bay View Condo Overlooking Pool in Great Mid-Town Location
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Hot Tub, Internet

2 Bedrooms8 Guests
10.0

Exceptional

33 reviews

$464
Average price / night
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Beautiful and Spacious Ocean Block Condo!!!  Amazing Bay and Ocean Views!!!
Beautiful and Spacious Ocean Block Condo!!! Amazing Bay and Ocean Views!!!
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

AC, Balcony, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms10 Guests
9.8

Exceptional

84 reviews

$462
Average price / night
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Perfect Bay, Beach and Pool Condo for a Family!
Perfect Bay, Beach and Pool Condo for a Family!
Condo
Ocean City, MD, 21842, United States
2.3k from Isle of Wight Bay center

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

1 Bedroom5 Guests
9.8

Exceptional

48 reviews

$231
Average price / night
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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 Isle of Wight Bay.

Where to stay in Isle of Wight Bay? Best neighborhoods & areas

Isle of Wight Bay Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 509 verified vacation rentals with a private pool in Isle of Wight 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 Isle of Wight Bay vary depending on the property size, location, and travel season. Rates typically start from around $141 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 Isle of Wight 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 Isle of Wight Bay often include additional features such as Private Pool, Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Isle of Wight 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.