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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Maryland

  5.  Isle of Wight Bay

Refine your search

Price per night

Amenity Filter

Rating

2906 Best Vacation Rentals with Pool in Isle of Wight Bay (Starting from $149)

Runaway Bay 810
Runaway Bay 810
House
Ocean City, MD, USA
1.6k from Isle of Wight Bay center

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

4 Bedrooms10 Guests
7.0

Good

1 reviews

$474
Average price / night
Check Availability
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
Check Availability
Runaway Bay 76
Runaway Bay 76
House
Ocean City, MD, USA
1.8k from Isle of Wight Bay center

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

3 Bedrooms10 Guests
6.8

Good

9 reviews

$149
Average price / night
Check Availability
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
Check Availability
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
Check Availability
Bayside Clean and Comfortable with a Pool 4 min walk to Beach and Boardwalk
Bayside Clean and Comfortable with a Pool 4 min walk to Beach and Boardwalk
Condo
Ocean City, MD, 21842, United States
1.9k from Isle of Wight Bay center

AC, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$276
Average price / night
Check Availability
Penguin Drive
Penguin Drive
Apartment
Isle of Wight Bay, Ocean City, Maryland, USA
1.9k from Isle of Wight Bay center

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

2 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$189
Average price / night
Check Availability
Makai Sunset Cove all-season indoor pool
Makai Sunset Cove all-season indoor pool
Apartment
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

2 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$316
Average price / night
Check Availability
Thunder Island 43B
Thunder Island 43B
Apartment
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

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

1 Bedroom8 Guests
New to Booking
$223
Average price / night
Check Availability
Spacious 3 Bedroom 3 Bathroom Townhome, Pool, and 30 Ft. Pier
Spacious 3 Bedroom 3 Bathroom Townhome, Pool, and 30 Ft. Pier
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$369
Average price / night
Check Availability
Thunder Island 75B
Thunder Island 75B
House
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

Sports/Activities, Air Conditioner, Pool, Internet, Security/Safety, View, Parking

1 Bedroom7 Guests
New to Booking
$250
Average price / night
Check Availability
Bayside Retreat w/ Dock, Pool Access & 10 Min Walk to Beach!
Bayside Retreat w/ Dock, Pool Access & 10 Min Walk to Beach!
House
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

3 Bedrooms8 Guests
9.0

Fabulous

43 reviews

$353
Average price / night
Check Availability
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
Check Availability
Newly Renovated Makai Condo!
Newly Renovated Makai Condo!
Apartment
Ocean City, MD, 21842, United States
2.0k from Isle of Wight Bay center

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

2 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$310
Average price / night
Check Availability
Bayside Beauty
Bayside Beauty
House
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

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

3 Bedrooms9 Guests
6.2

Good

6 reviews

$399
Average price / night
Check Availability
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
Check Availability
Gullway Getaway
Gullway Getaway
House
Ocean City, MD, USA
2.0k from Isle of Wight Bay center

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

3 Bedrooms10 Guests
7.6

Good

7 reviews

$317
Average price / night
Check Availability
Ocean City Bayside Condo, Newly Renovated
Ocean City Bayside Condo, Newly Renovated
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$298
Average price / night
Check Availability
Gullway Townhouse 2823 townhouse
Gullway Townhouse 2823 townhouse
House
Ocean City, MD, USA
2.1k from Isle of Wight Bay center

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

3 Bedrooms8 Guests
4.0

Review score

2 reviews

$285
Average price / night
Check Availability
Waterfront bayside condo with large, private balcony and amazing views!
Waterfront bayside condo with large, private balcony and amazing views!
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
9.6

Exceptional

17 reviews

$285
Average price / night
Check Availability
Wight Bay North #439
Wight Bay North #439
Apartment
Ocean City, MD, USA
2.1k from Isle of Wight Bay center

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

2 Bedrooms7 Guests
8.2

Very Good

6 reviews

$280
Average price / night
Check Availability
Wight Bay 443 is in the Heart of OC and close to everywhere you want to be!
Wight Bay 443 is in the Heart of OC and close to everywhere you want to be!
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
9.6

Exceptional

9 reviews

$268
Average price / night
Check Availability
Bayfront Three Bedroom Condo with Awesome Views
Bayfront Three Bedroom Condo with Awesome Views
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

3 Bedrooms9 Guests
9.6

Exceptional

5 reviews

$702
Average price / night
Check Availability
Bright Townhome on the Bay with Pool, Short Walk to Beach and Boardwalk
Bright Townhome on the Bay with Pool, Short Walk to Beach and Boardwalk
House
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$376
Average price / night
Check Availability
2-bedroom Condo in OCMD Centrally Located, 2 Parking Spaces, Pool, and Grills
2-bedroom Condo in OCMD Centrally Located, 2 Parking Spaces, Pool, and Grills
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

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

2 Bedrooms7 Guests
New to Booking
$227
Average price / night
Check Availability
Bayfront Condo - Family Friendly - 3BR/2.5 Bath
Bayfront Condo - Family Friendly - 3BR/2.5 Bath
Condo
Ocean City, MD, 21843, United States
2.1k from Isle of Wight Bay center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$442
Average price / night
Check Availability
Wight Bay 254 by Seaside Vacations & Sales
Wight Bay 254 by Seaside Vacations & Sales
Condo
Ocean City, MD, 21842, United States
2.1k from Isle of Wight Bay center

AC, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$358
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 Isle of Wight Bay.

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

Isle of Wight Bay Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2906 verified vacation rentals with a pool in Isle of Wight 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 Isle of Wight Bay vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $149 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Isle of Wight 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 Isle of Wight Bay welcome pets. Currently, 1 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 Isle of Wight Bay often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Isle of Wight 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.