
Holiday houses in Isle of Wight Bay
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Top-rated holiday rentals in Isle of Wight Bay
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Gorgeous Beachfront! King Bed, Direct Ocean View!
Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

The Oliver House
This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Stunning private waterfront suite
Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Camelot
HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

Light and Airy Oceanfront Condo with Large Porch
Wake up to the sound of the waves crashing outside your window and finish off your days relaxing on the private balcony as you watch the moon rise over the ocean. Come find your serenity by the sea in our modern oceanfront condo. Located in midtown Ocean City, you can keep your car parked in our dedicated spot and walk to many of the towns best restaurants, bars, and entertainment as well as the Convention Center and Performing Arts Center. Morning beach strolls and evening sips await :)

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf
Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets may apply.

Bayfront - Walk to Beach & Boardwalk - King Bed
Welcome to our Home Beach Resort! Just a 5-minute walk to Ocean City Beach, boardwalk, bars, restaurants, and amusement parks. 🌅 Bayfront Views – Enjoy stunning sunrises from the master bedroom and sunsets on the bay. 🏡 Comfort & Convenience – Fully furnished home with a private gated boardwalk. 🎣 Outdoor Fun – Fish and crab right in front of the house! ☕ Modern Amenities – Fully equipped kitchen, Keurig coffee maker, WiFi-6. Book now for the ultimate Ocean City getaway!

Assateague, Golf, Ocean City, all Within Minutes!
Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

Ocean Side 1BR / 1.5BA Renovated Modern Condo
Ocean Side! Two minute walk to the beach! Fully renovated. Bright, modern, clean condo. First floor. Located in the heart of Ocean City ( Midtown ) in walking distance from restaurants, bars, shops, and public transportation. Brand new appliances and furniture. Free WiFi, King Size Bed, 65" TV (living room) & 50" TV bedroom. Pullout Queen Sofa, Brand New Full Bathroom + Half Bathroom, Washer and Dryer in the unit. Keurig Coffee, Private balcony. Free Parking Space.

Bright and Airy Oceanside Condo
Wake up to stunning ocean sunrises from your private balcony and enjoy bay sunsets just outside your front door. This oceanside condo in midtown Ocean City, MD is steps from the beach!! Beachside with no street to cross. Park your car for free in our covered lot. Enjoy a walkable location near top restaurants, bars, nightlife, and attractions like Seacrets, Fager’s Island, Macky’s, breakfast at barn 34 and mini golf. Ideal for a convenient Ocean City beach vacation.

Secluded Waterfront - Beach 15mi, Kayaks, Firepit
Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

Luxurious Bay Front Condo
Escape to luxury at our bay-front condo, just 2 blocks from the beach. This tranquil retreat is perfect for families, offering stunning views and modern comforts. Enjoy nearby sandy shores, and unwind in a serene setting. Ideal for creating cherished memories. Optional boat slips available please message for details. (We do not rent to seniors for senior week)
Popular amenities for Isle of Wight Bay holiday rentals
Other great holiday rentals in Isle of Wight Bay

Cozy beach home away from home!

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White Marlin Cottage>HOT TUB<

323 Yacht Club | Peaceful Bay greenery retreat

Hot Tub & Pool Table Waterfront Home | 4King Beds

Bayside Condo in Midtown Ocean City MD

Looney Dunes

Waterfront Condo on 28th St.! BS#6
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- Broadkill Beach
- Rehoboth Beach
- Assateague State Park
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Willow Creek Winery & Farm
- Northside Park
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- Delaware Seashore State Park
- Jolly Roger Amusement Park
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- Roland E Powell Convention Center
- Wildwoods Convention Center
- Mariner's Arcade
- Funland
- Dewey Beach Access
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