Holiday houses in Isle of Wight Bay

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Top-rated holiday rentals in Isle of Wight Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Condo in Ocean City
4.99 out of 5 average rating, 146 reviews

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!!

Top Guest favourite
Guest suite in Ocean Pines
4.95 out of 5 average rating, 417 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
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 533 reviews

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 :)

Guest favourite
A waterfront backyard features sandy areas lined with a white picket fence. A picnic table is positioned on the beach, facing the calm waterway. Houses are visible along the banks, framed by trees and distant structures under a soft evening sky.
Home in Ocean Pines
4.91 out of 5 average rating, 209 reviews

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!

Superhost
An aerial view of a marina with multiple boats docked along a well-maintained pathway. The surrounding residential community and parking area are visible, as sunlight reflects off the peaceful water, highlighting the scenic environment.
Townhouse in Ocean Pines
4.88 out of 5 average rating, 108 reviews

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.

Top Guest favourite
Apartment in Ocean City
4.98 out of 5 average rating, 106 reviews

Handful of Beach Heaven!

In the center of it all! Newly Offered, Beautifully Renovated Condo Only Steps to the Beach, Dinner or Putt Putt! Walking distance to numerous restaurants, Seacrets Nite Club, the Convention Center, Dumsers Ice Cream and More! Fully Equipped Kitchen in case you want to hide away for the weekend. Queen Bed and Queen Sleeper Sofa. Outside Storage for Beach Necessities, where you'll find a Beach Umbrella and Chairs for your use. 45th Street Location. This has it all!

Top Guest favourite
Condo in Ocean City
4.96 out of 5 average rating, 181 reviews

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.

Top Guest favourite
The open concept living area combines a kitchen, dining space, and lounging area, featuring light-toned cabinetry and modern appliances. A round dining table with two stools is positioned near a window, while a cozy couch and media console are arranged for comfort and convenience.
Apartment in Ocean City
4.92 out of 5 average rating, 133 reviews

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.

Guest favourite
A spacious living area features a large sectional sofa and two armchairs, complemented by a coffee table and area rug. Natural light floods through sliding glass doors that lead to a private deck, with water views visible from the room. Decorative wall art adds a calming touch.
Townhouse in Ocean City
4.91 out of 5 average rating, 293 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.

Superhost
Townhouse in Ocean City
4.75 out of 5 average rating, 4 reviews

Luxury Bayfront Retreat - Exclusive Waterfront

Experience elegant coastal living with panoramic sunset views over Assawoman Bay from every level. Nestled in one of Ocean City’s premier waterfront boating communities, this upscale retreat offers a peaceful escape just minutes from the beach, Boardwalk, dining, and entertainment. Ideal for families, couples, and discerning travelers seeking a refined vacation experience in a quiet luxury setting.

Top Guest favourite
A well-lit living area features a comfortable seating arrangement and a flat-screen TV mounted on the wall. Natural light floods in through sliding glass doors that open to a private balcony, enhancing the spacious feel of the room. A small table and plant add a touch of decor.
Apartment in Ocean City
4.96 out of 5 average rating, 114 reviews

Oceanside Condo Steps From Beach

Escape to our stylish, surf-inspired ocean view condo, just steps from the beach! This bright, airy retreat comfortably sleeps 4 and features a private balcony to watch the sunrise, a fully equipped kitchen, and a luxury king bed. Perfect for a relaxing beach getaway, you'll enjoy modern amenities and direct beach access via a sandy path. Your unforgettable coastal escape awaits!

Guest favourite
A balcony railing frames a wide view of the ocean, where gentle waves meet a sandy shore under a clear blue sky with scattered clouds. The horizon line is visible, enhancing the sense of openness and tranquility.
Condo in Ocean City
4.9 out of 5 average rating, 130 reviews

One Bedroom Beachfront Apartment Mid-Town

Midtown serves as the intersection between the vibrant inlet and boardwalk and the serene North Ocean City. In addition to stunning views of the beach and impressive hotels and condos, it also provides easy access to a wide range of activities, restaurants, shops, and attractions that cater to individuals of all age groups.

Popular amenities for Isle of Wight Bay holiday rentals