Vacation rentals in Isle of Wight Bay

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Top-rated vacation rentals in Isle of Wight Bay

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

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Top guest favorite
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, 149 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!!

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Top guest favorite
The front exterior of a charming two-story house is shown, featuring a pitched roof and light-colored siding. A bright blue door welcomes visitors. A white picket fence encloses the front yard, which is neatly landscaped with greenery and flowering plants.
Home in Ocean City
4.97 out of 5 average rating, 106 reviews

Dolores by the Sea- Family Groups ONLY

This recently remodeled 1950's house is walking distance to the beach, boardwalk, & fabulous restaurants. Tucked away from the hustle & bustle in a quiet neighborhood this cozy home is the perfect place to relax after a fun filled day at the beach. This home has 4 bedrooms & up to 7 beds. With a wheelchair ramp & a fenced in yard this house is perfect for family gatherings & making memories. Please note that due to neighborhood restrictions we cannot book to unrelated renters under 27 years old

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Top guest favorite
Apartment in Ocean City
4.92 out of 5 average rating, 24 reviews

Your Beachside Studio Getaway

Welcome to your perfect seaside getaway! This studio sits just steps from the sandy shore, offering ocean views and the soothing sounds of the waves. Inside, you’ll find a comfy queen-sized bed, pull out sleeper couch with plush linens, and a kitchenette equipped with all the essentials for cooking. Large windows flood the room with natural light where you can sip your morning coffee while watching the sunrise over the water. Perfect for solo travelers or couples seeking a tranquil beach escape!

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Top guest favorite
Guest suite in Ocean Pines
4.95 out of 5 average rating, 419 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!

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Top guest favorite
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, 223 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

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Top guest favorite
A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.
Condo in Ocean City
4.88 out of 5 average rating, 142 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

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Guest favorite
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
4.91 out of 5 average rating, 138 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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Top guest favorite
A cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.
Home in Ocean Pines
4.97 out of 5 average rating, 114 reviews

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

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Guest favorite
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, 294 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.

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Guest favorite
An oversized balcony features comfortable seating with deep blue cushions. A glass-top table sits between the chairs. Below, the water view showcases boat traffic, while string lights add a gentle ambiance. The surrounding area includes other residential units and docks.
Condo in Ocean City
4.88 out of 5 average rating, 276 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!

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Top guest favorite
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, 117 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!

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Top guest favorite
A spacious living room features light-colored furniture with striped patterns, complemented by a neutral decor. A modern fireplace is set beneath a wall-mounted television, and the kitchen area is visible, showcasing cabinetry and a decorative anchor. Natural light flows through sliding doors leading to a balcony.
Home in Ocean City
4.99 out of 5 average rating, 69 reviews

Luxurious Bay Front Condo

Escape to luxury at our bay-front condo, just 2 blocks from the beach. This tranquil retreat is perfect for families, offering stunning views and modern comforts. Enjoy nearby sandy shores, and unwind in a serene setting. Ideal for creating cherished memories. Optional boat slips available please message for details. (We do not rent to seniors for senior week)

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Popular amenities for Isle of Wight Bay vacation rentals