Vacation rentals in Isle of Wight Bay

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Top-rated vacation rentals in Isle of Wight Bay

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Guest favorite
Apartment in Ocean City
5 out of 5 average rating, 32 reviews

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!

Top guest favorite
Home in Ocean City
5 out of 5 average rating, 47 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 favorite
Home in Ocean City
4.97 out of 5 average rating, 78 reviews

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

Top guest favorite
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, 528 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 :)

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, 104 reviews

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marinaโ€™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.

Guest favorite
A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.
Home in Ocean Pines
4.94 out of 5 average rating, 18 reviews

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Top guest favorite
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, 50 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. ๐ŸŒ… Bayfront Views โ€“ Enjoy stunning sunrises from the master bedroom and sunsets on the bay. ๐Ÿก Comfort & Convenience โ€“ Fully furnished home with a private gated boardwalk. ๐ŸŽฃ Outdoor Fun โ€“ Fish and crab right in front of the house! โ˜• Modern Amenities โ€“ Fully equipped kitchen, Keurig coffee maker, WiFi-6. Book now for the ultimate Ocean City getaway!

Top guest favorite
The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.
Home in Berlin
4.98 out of 5 average rating, 103 reviews

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

Top 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
4.92 out of 5 average rating, 129 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, Fagerโ€™s Island, Mackyโ€™s, breakfast at barn 34 and mini golf. Ideal for a convenient Ocean City beach vacation.

Top guest favorite
A modern living area is presented, featuring a plush gray sofa and a minimalist coffee table. A large television is mounted on the wall opposite the seating. Natural light filters through sliding glass doors, which lead to a private balcony with a small table and chairs.
Condo in Ocean City
4.99 out of 5 average rating, 341 reviews

Steps to the Beach, Ocean View 1BR, Renovated

Steps to the beach! Fully renovated, bright, modern, clean condo with a balcony view of the ocean. Quiet North Ocean City location with walking distance to restaurants, bus, 7-11, Mini golf course, movie theater, parks, etc. Brand new appliances and furniture. Free WiFi, King Size Bed, 60" & 40" TVs. Pull Out Queen Sofa, Brand New Full Bathroom. Washer and Dryer in the unit. Keurig Coffee Station, iPhone Charging station. Private balcony. Free Parking Space.

Top guest favorite
A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.
Home in Newark
5 out of 5 average rating, 120 reviews

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ftยฒ (209 mยฒ) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. โ˜… "A private and tranquil setting where it is impossible not to relax and appreciate natureโ€ฆ Wish I had booked an extra day!" Add us to your wish list by clicking the โค๏ธ in the upper-right corner.

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
4.98 out of 5 average rating, 66 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)

Popular amenities for Isle of Wight Bay vacation rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Isle of Wight Bay