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, 137 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
Home in Ocean City
5 out of 5 average rating, 45 reviews

Bayside - Waterfront - Dock - Quiet Area

The Good Life is home to all that OCMD has to offer. This bayfront home is a short drive to beautiful Assateague Island and central OCMD. Freshly renovated with brand new furniture and stunning finishes in the kitchen and baths. Formal dining area opens to kitchen; screened in porch with ceiling fan and deck with grill, picnic table, outdoor shower and boat dock with quick access to the bay. House includes beach chairs; wagon; washer and dryer. The perfect place to create vacation memories.

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, 521 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 :)

Top Guest favourite
Condo in Ocean City
5 out of 5 average rating, 24 reviews

Breezy Point #301 - Rooftop Deck Panoramic Sunsets

Welcome to Your Bayside Escape at Breezy Point! Step into this fully remodeled bayside condo, modern upgrades throughout. 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!

Top Guest favourite
Vibrant orange and yellow lilies are in full bloom, positioned in the foreground along a pathway. The path leads towards a waterfront area, with chairs visible in the background. A clear sky and soft sunlight enhance the peaceful ambiance of the setting.
Townhouse in Ocean City
4.96 out of 5 average rating, 48 reviews

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!

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, 123 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.

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Guesthouse in Ocean Pines
5 out of 5 average rating, 4 reviews

Coastal Retreat near the beach

Kick back and relax in this calm, stylish space just 15 minutes from Ocean City MD beaches. The unit has marsh and water views of Assawoman Bay/Manklin Creek. Located across the bay from Ocean City , MD you are close to the action but can retreat back to a quiet sanctuary when you are looking for some relaxation away from the beach crowds. If you like nature, frequent visitors include, deer, fox, blue heron, egrets, bald eagles, owls and many other birds.

Top Guest favourite
A charming cottage exterior is showcased, featuring a wooden deck surrounded by white railings. Steps lead up to the entrance, bordered by smooth landscaping and ornamental grasses. Shadows from nearby trees create a serene ambiance against a cloudy sky.
Cottage in Selbyville
4.96 out of 5 average rating, 76 reviews

Country Cottage -7 Miles from Fenwick Island Beach

Welcome to PopPop’s Place. This is a cozy, 1,000 sq. ft. 1 bedroom 1 bath cottage that has been on our family’s 20 acre property for more than 60 years. It is located 7 miles west of Fenwick Island, DE and North Ocean City, MD. While we are close to the beaches and attractions, we are also close to multiple golf courses, inland bays for kayaking, crabbing, fishing, entertainment at Freeman Stage-Bayside and many other fun vacation activities.

Guest favourite
The living area features a light wood floor with a cozy sofa, a coffee table, and a television on a stand. A kitchen island with bar stools separates the space, while a door leads to a patio area, allowing natural light to fill the room.
Condo in Ocean City
4.95 out of 5 average rating, 169 reviews

Lovely 1 bedroom condo/only 2 blocks to the beach

Enjoy a wonderful experience at this centrally-located place only two blocks away from the beach and Ocean City boardwalk. Newly remodeled condo in a great location within a walking distance to many amazing restaurants and bars, convenience stores, amusement park, mini-golf, boutiques, playground...

Top Guest favourite
The charming carriage house features a light-colored exterior with white trim and a metal roof. Two garage doors and multiple windows offer ample natural light, while a gravel driveway provides access to the entrance. Surrounding trees add a touch of greenery to the serene setting.
Guest suite in Berlin
4.97 out of 5 average rating, 659 reviews

Ayers Creek Carriage House

Our beautiful carriage house is located on 5 pristine acres along, scenic Ayers Creek, offering year round beauty. Only minutes from Assateague Island, Berlin, and Ocean City. Serene with abundant wildlife. Ideal oasis for outdoor enthusiasts. Worcester County Maryland Rental License #1324

Guest favourite
A tranquil beach scene is captured, featuring gentle waves lapping at the shoreline. A wooden fence is positioned in the foreground, separating the sand from the grassy dunes. The sky displays a soft gradient of colors, transitioning from light pink to blue, as the sun sets on the horizon.
Apartment in Ocean City
4.93 out of 5 average rating, 44 reviews

“Lei’d Back” | Pet Friendly & Steps to the Sand

Just steps from the Ocean City beach! This comfy one bedroom, one bathroom condo features fresh paint, comfy new furniture, and a modern kitchen-perfect for couples or small families. Relax and enjoy your stay in Ocean City with a local manager nearby to help with anything you need!

Top Guest favourite
An open-concept living area showcases a spacious sofa arranged around a light-colored coffee table, accented with decorative shells. A dining area with white bar stools and a fully equipped kitchen are visible in the background, along with coastal-themed decor and soft natural light.
Condo in Ocean City
4.98 out of 5 average rating, 116 reviews

Oceanside Charm, desirable midtown Ocean City, MD

Steps to the beach and across the street from the Convention Center, this mid-town Ocean City Condo is fully loaded with everything you need for cooking, sleeping, hanging out, and hitting the beach. Email me with questions...I'm an open book!

Popular amenities for Isle of Wight Bay holiday rentals