Holiday rentals in Isle of Wight Bay

Luxurious Ocean Block condo

Enjoy a stylish experience at this centrally-located place. The exquisite and beautiful updated condo offers a combination of luxury, comfort and elegance with a modern look. Located midtown, across the street from Secrets, just a few steps away from the beach! The ideal place for a vacation that offers a fully brand new equipped kitchen, washer and dryer, dishwasher and WiFi. King size bed and a sleeper sofa in the living room. Half bathroom attached to the bedroom. Must be at least 25 to book!

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!!

**Beautiful newly renovated OC MD water view home*

Beautiful Bay view ground floor unit steps away from the water, 1 free parking spot available for guests and tons of street parking comfortable for 2 people for a long stay and 4 for a weekend getaway Located in the middle of all Ocean city major attractions Walking distance to the beach and Jolly Roger Amusement water Park and tons of other activities and restaurants. 6 min away from famous Seacrets, Macky’s & Fish Tales 8 min drive to OC famous board walk & downtown 15 min to Shopping Outlets

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!

Assateague, Golf, Ocean City all Within Minutes.

Welcome to The Cottage @ Assateague Oasis – a luxury, peaceful retreat. Enjoy spa-like primary suite, gourmet kitchen, unique industrial design, and family-friendly comfort. Just 1.5 miles from Assateague Island and .5 miles from 3 top-rated golf courses. Located in a quiet neighborhood, large 1+ acre lot. hosted by Kevin & Mia, well-seasoned Airbnb hosts. Perfect for families, golfers, and beach lovers seeking a stylish escape. Linens and towels included! Book your memorable vacation today!

Central AC, Luxury Bathrooms, 4 blocks to Beach!

Welcome to our beautifully renovated condo in Ocean City, MD! Central AC added in Spring 2026 makes this one of the most comfortable condos in Ocean City. No more noisy "wall-rattler" AC units. When you stay here, you will enjoy two renovated luxury bathrooms, new bedroom floors and furniture, new living room couches, updated recessed lighting, and a full kitchen. We have just the right mix of luxury and comfort in this space. You will be able to relax with all the essentials during your stay.

Ocean Pines Yacht Club Getaway Waterview

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

The Red Barn Suite

Stay at our brand new barn suite located on our family farm and enjoy a peaceful and quiet country setting. Come back after the beach (just 8 miles away) and cook on the grill and relax on the private deck overlooking the bamboo and pond. Plenty of room inside with a large living room/ full kitchen, bedroom, and bathroom with a custom tile shower. Our modern and cozy barn suite is just minutes away from Bayside Resort, Restaurants, Assowoman Wildlife Refuge, and Delaware and Maryland Beaches.

Breezy Point #305 - Rooftop Deck Panoramic Sunsets

Welcome to Your Bayside Escape at Breezy Point! Step into style at this sleek bayside condo where modern comfort meets bayside views. Relax on the rooftop terrace and enjoy stunning sunset views and the fresh air. Tucked just off 28th Street, you're near restaurants, shops and quick bites. The boardwalk and beach are an easy walk or a quick drive away. A comfortable and convenient home base for couples and families. Hosting a bigger group? Ask about our other units in the same building!

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Oceanfront 1 Bdrm-Sleeps 4-Linens-Pool-WiFi

Howzit! Catch the wave of relaxation at Aloha House, nestled in the rad Pyramid condo building. This sweet 1-bedroom, 1.5-bathroom pad is your ultimate beachside escape, comfortably sleeping up to 4 of your crew. The bedroom's got a king bed for max comfort, and there's a queen sofa bed in the living room, perfect for chilling by the electric fireplace. With smart TVs in both the living room and bedroom, you'll have all the entertainment you need! There's gig speed WiFi too!