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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Guest favourite
Condo in Ocean City
5 out of 5 average rating, 12 reviews

Downtown Condo, Parking, Walk to Beach & Boardwalk

Modern 2BR/2BA downtown Ocean City condo with bay view, balcony, elevator, pool, and parking. Sleeps 6 with 1 king and 2 queen beds. Walk about 1,000 ft to the inlet beach, boardwalk, rides, pier, dining, festivals, and downtown events. Enjoy a full kitchen, dishwasher, washer/dryer, smart TVs, WiFi, linens, bath towels, beach towels, chairs, umbrella, and cooler. Includes 1 assigned parking space plus 1 shared first-come space with passes. Perfect for families, couples & event-goers year-round.

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!!

Guest favourite
Apartment in Ocean City
5 out of 5 average rating, 9 reviews

The "O.C. Crab House" on 32nd Street

Short walk to both bayside AND the beach! Couples LOVE this 1 bedroom/ 1 bath efficiency condo. Queen Size spaciously sleeps two/drop down sofa sleeps 1 adult/youth. Included in minimum 3 night rental: linens/bedding/towels/paper goods/soaps/trash bags. Fully stocked kitchen: w/ dishwasher, microwave, coffee maker/complimentary k cups, washer, dryer in unit /private balcony/wifi/tv. At 33rd and it's two blocks to the sand. Just across 32nd from Jolly Rogers. Non-Smoking/ Non-Vaping/No pets

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
A spacious bedroom features natural wood paneling and exposed beams. A comfortable bed is dressed in a patterned blanket, while large glass doors open to a private balcony with ocean views. Soft blue curtains frame the entrance, allowing natural light to fill the room.
Home in Ocean City
4.97 out of 5 average rating, 32 reviews

Seahaven

Our rowhouse is direct OCEAN front and steps from the beach. Walk in on ground level and up to beachfront. Go up one more level to two large bedrooms, one with stunning direct ocean front views. Watch for dolphins and whales from the upstairs balcony or stay downstairs and watch the kids play outside the backdoor. The ocean is just on the other side of the sand dune. Oceanhaven is located in the low density stretch of Ocean City, with the least crowded and widest sections of beach.

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
Condo in Ocean City
4.96 out of 5 average rating, 167 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, 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.

Superhost
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
Condo in Ocean City
4.91 out of 5 average rating, 144 reviews

Cozy Beach Front Condo with Modern Amenities.

Our condo is located on a quiet street, just steps away from the oceanfront. The perfect beach getaway at our cozy condo, situated across the street from Seacrets, mini, restaurant, an array of entertainment options. Accommodates up to 4 guests, features well-stocked kitchen, 2 smart TVs for streaming, WiFi, A/C, washer/dryer, dishwasher, microwave, hair dryer, iron, kitchenware. Relax on the balcony, 1 designated parking space, outdoor shower after.

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 serene ocean scene captures gentle waves lapping at a sandy shore. The horizon is lined with soft, multicolored clouds reflecting the light of a fading sun, blending shades of blue, orange, and pink across the sky.
Condo in Ocean City
4.93 out of 5 average rating, 28 reviews

La Pescadora - Cozy. Coastal. Completely Yours.

La Pescadora is an oceanfront escape designed for calm, effortless stays. A cozy + stylish 2 bed/2 bath condo on 80th Street in Ocean City, MD | Private beach area + path | Quiet with easy access to all OC has to offer La Pescadora, or Fisherwoman, honors the courageous women soul- and sea-farers throughout history.

Popular amenities for Isle of Wight Bay holiday rentals