Holiday houses in Isle of Wight Bay

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Top-rated holiday rentals in Isle of Wight Bay

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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, 133 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!!

Guest favourite
Condo in Ocean City
5 out of 5 average rating, 10 reviews

3 Bdrm Condo Bayfront w/Boat Slip, Calling Concert

Bayfront BREATHTAKING southern view perfect for relaxing, swimming, kayaking, paddle board, claming, crabbing and fishing. Boat slip w/dock. Large porch 10 feet from the water. 3 bedrooms- 2 w/ queen beds, 1 w/ 2 twin beds 2 bathrooms- one walk in shower, one tub. Fully equipped kitchen to prepare anything from a snack to feast. Wash/Dryer Off street parking for 2 cars Use of beach chairs, umbrellas. We do not rent to anyone under the age 25 3 block walk to beach, 35min walk to Calling Concerts

Top Guest favourite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines
4.97 out of 5 average rating, 218 reviews

Water view at Ocean Pines Yacht Club Condo

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

Guest favourite
A spacious living room features a large flat-screen TV mounted on a white entertainment unit. The room is enhanced by pine plank ceilings and offers expansive ocean views through sliding glass doors that lead to a private balcony.
Condo in Ocean City
5 out of 5 average rating, 21 reviews

Ultra Luxe Oceanfront Escape w/Breathtaking Views!

Enjoy a rare beach-house feel from this renovated first-floor oceanfront condo in North Ocean City. Set just one level up, the unit offers a spectacular perspective of the dunes, beach, ocean, and waves breaking right outside. Enjoy direct beach access, two reserved parking spaces, elevators, linens and towels, a heated indoor pool and hot tub, and a new 4,000 SF ocean-view sun deck. Inside, this warm coastal retreat sleeps 8 with pine ceilings, luxury finishes, and private balcony views.

Top Guest favourite
A modern living room features a comfortable sectional sofa in neutral tones, paired with a rustic wooden coffee table. A television is mounted above a stone accent wall. Glass doors open to a balcony, allowing natural light to fill the space.
Condo in Ocean City
4.95 out of 5 average rating, 127 reviews

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!

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, 517 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
A comfortable living area features a sectional sofa adorned with patterned cushions, paired with a coffee table at its center. A dining table is positioned nearby, complemented by decorative wall art and natural light filtering through sheer curtains. Ceiling fans add a refreshing touch to the space.
Apartment in Ocean City
5 out of 5 average rating, 29 reviews

Bayside Breeze! 6 Guests, 2 bedrooms: 1 bathroom

Welcome to your perfect beach getaway in Ocean City! This newly renovated, beach-themed 2-bedroom, 1-bathroom apartment is the ideal place to relax, unwind, and enjoy everything this vibrant coastal town has to offer. Step inside and feel the beach vibes instantly. This apartment features bright, airy decor with coastal colors, brand new furniture and fully equipped kitchen so you can whip up anything from quick snacks to full dinners. Short walk to Jolly Rogers and boardwalk.

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, 119 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.

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.

Top Guest favourite
A bright living space features a large blue sectional sofa with accent pillows and a stylish coffee table. A dining area with a white table and four chairs is situated nearby. A mounted television is visible on the wall, alongside light-colored finishes and decorative wall art.
Condo in Ocean City
4.94 out of 5 average rating, 125 reviews

Lovely Ocean Block 1 BR near Convention Center!

Brand new beautiful renovation just completed last year!! 1 BR ocean block condo on 40th St, across from convention center & half a block from ocean & great, uncrowded section of beach. Easy self check in with key pad - no keys! Decor is updated and has brand new granite countertops, beautiful tiled bathroom, new appliances & furniture, comfortable bed & sofa, Wifi and central air. Your home away from home!

Guest favourite
The exterior of a single-story cottage is visible, featuring light green siding and white shutters. A welcoming front porch is flanked by lush shrubs and greenery. A well-kept lawn and flower beds complement the home, set against a backdrop of trees.
Home in Berlin
4.98 out of 5 average rating, 108 reviews

3 Bed 2 Bath House in the Heart of Berlin

Walking distance to downtown Berlin! This cute, cozy, cottage offers a large master bedroom with a king size bed and bath, and two guest bedrooms with a queen size bed, and a bathroom across the hall. Located in America’s Coolest Small Town featuring many shops, restaurants, and bars with a close by brewery. Ocean City beaches and Assateague Island National Seashore are about 10-15 minutes away.

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

67th St. 3BR condo, 2 Pools*FREE Linens & Towels!

Beautifully decorated 3 bedroom & Sleeping 8, Parking for 2 vehicles, one space is covered. FREE Linen & Towel package! Includes 6 beach chairs & a beach cart too. Check in directly at condo, No Stopping at a rental office, Keyless Entry. ***NO Groups, No high school groups, no bachelor or bachelorette groups. Family Rental only. ***

Popular amenities for Isle of Wight Bay holiday rentals