Holiday rentals in Isle of Wight Bay

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Top-rated holiday rentals in Isle of Wight Bay

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Guest favourite

Apartment in Ocean City

4.98 out of 5 average rating, 160 reviews

Family Condo Oceanside in Midtown OC

Oceanside, sleeps 6, 2 full baths, 2 parking spots, full kitchen, barstools, table, 6 person couch, and balcony views of bay and beach. Set up for families, slower midtown feel. Easy, safe beach access! 3rd floor walk up. Expect a quality, local AirBnB experience from Superhosts! No noisy neighbors, downtown partying, or parking difficulties. NEW for 2025: - Fridge/freezer - Patio furniture - Linens & Decor - Bunk room Smart TV The space is fully loaded to make packing a breeze! See reviews!

Guest favourite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 377 reviews

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!

Top guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 168 reviews

Getaway in Ocean Pines

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Top guest favourite

Home in Ocean Pines

4.98 out of 5 average rating, 120 reviews

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!

Guest favourite

Apartment in Ocean City

4.96 out of 5 average rating, 275 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Guest favourite

Apartment in Ocean City

4.95 out of 5 average rating, 191 reviews

Bayside Bliss - Renovated Downtown Condo w/ Porch

Welcome to Bayside Bliss, a stylish 2BR / 2BA top floor condo in Downtown OC. Relax in the oversized living room, stream your favorite shows and music to any of the smart tvs, or watch the sunset on the porch. The fully equipped kitchen, washer & dryer, and two full bathrooms will make your stay feel like home. Just a short walk to some of OC's best restaurants, nightlife, the boardwalk, and the beach. Steps away from the White Marlin Open weigh-ins and OC Air Show

Superhost

Apartment in Ocean City

4.91 out of 5 average rating, 308 reviews

CANAL FRONT Wi-Fi, Roku, Netflix, boatslip, pool

BEAUTIFUL WATER VIEW ON 28 STREET.1 bedroom apartment with full kitchen and bath. Bedroom has 2 full size beds, boat slip and boat ramp. 1 onsite parking spot included, plenty of parking available in front of building. Public transportation close by. Walk to beach,boardwalk, restaurants, miniature golf, go cart tracks, Jolly Rogers Amusement and Water park. Free WiFi, Netflix, Hulu, and Roku to connect to your streaming services. Coded entrance. Beach gear.

Guest favourite

Townhouse in Ocean City

4.91 out of 5 average rating, 240 reviews

Bayfront Townhouse: Fishing, Sunsets & Family Fun!

Escape to this stunning, updated bayfront townhouse in midtown Ocean City! Featuring 3 bedrooms with 3 ensuite bathrooms, enjoy breathtaking sunsets from your private deck. This entertainer's dream offers a spacious open layout with a gourmet kitchen and waterfall countertops. Benefit from two assigned parking spots, fish directly off the back deck pier, a local favorite fishing spots, you'll love the waterfront access and relaxing atmosphere.

Top guest favourite

Guest suite in Ocean City

4.98 out of 5 average rating, 367 reviews

The Elbridge Bayfront Studio

The Elbridge is a luxury studio apartment in downtown Ocean City. Beautiful bay view from studio windows. This bayside studio includes parking, a private garden entrance, and luxurious king bed. Located 4 blocks from the beach, the space is in a downtown residential neighborhood. Additionally included are bikes, bodyboards, beach chairs and a beach umbrella. Walking distance to delicious local restaurants, the boardwalk, and the beach!

Guest favourite

Apartment in Ocean City

4.89 out of 5 average rating, 221 reviews

Bayside Retreat in the Heart of Ocean City!

Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!

Guest favourite

Apartment in Ocean City

4.9 out of 5 average rating, 134 reviews

Ocean Side Condo-Steps From The Beach!

Enjoy a relaxing getaway at our Ocean Side condo. Just steps from the beach, our condo is centrally located on 44th St. Within walking distance of the Convention Center, Seacrets, 44th St. Taphouse, Mini Golf, and many other restaurants and shopping. Fully furnished, updated, clean, and modern. Washer/Dryer in unit.

Guest favourite

Flat in Ocean City

4.92 out of 5 average rating, 428 reviews

Private suite .5 mile from beach/no shared spaces

This spacious, private master suite is perfectly located on 116th street, half a mile from the beach and within walking distance to tons of shops and restaurants! Complete with a full bathroom, mini fridge, microwave, outdoor shower, and patio area, this cozy room is perfect for a relaxing beach getaway.