Holiday houses in Isle of Wight Bay

4.98 out of 5 average rating, 160 reviews

Family Condo Oceanside in Midtown OC

Oceanside, sleeps 6, 2 full baths, 2 parking spots, full kitchen, barstools, table, 6 person couch, and balcony views of bay and beach. Set up for families, slower midtown feel. Easy, safe beach access! 3rd floor walk up. Expect a quality, local AirBnB experience from Superhosts! No noisy neighbors, downtown partying, or parking difficulties. NEW for 2025: - Fridge/freezer - Patio furniture - Linens & Decor - Bunk room Smart TV The space is fully loaded to make packing a breeze! See reviews!

4.96 out of 5 average rating, 73 reviews

Gorgeous New Beachfront! King Bed, Direct Sea 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!!

4.97 out of 5 average rating, 167 reviews

Condo in Ocean Pines

Getaway in Ocean Pines

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

4.98 out of 5 average rating, 120 reviews

Home in Ocean Pines

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

4.96 out of 5 average rating, 448 reviews

Townhouse in Ocean City

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 :)

4.89 out of 5 average rating, 71 reviews

Apartment in Ocean City

Bright and Airy Oceanside Condo

Watch the sunrise over the ocean from your private balcony and end your day watching a gorgeous sunset over the bay from your front door! Come have it all while staying in this beautiful condo. Situated in desirable midtown Ocean City, MD and conveniently located ocean side so you never have to cross the street to get to the beach! Dinner plans? Keep your car parked for free and walk to the towns best restaurants, bars and entertainment like Seacrets, Fagers Island, Macky's...and more!

4.96 out of 5 average rating, 274 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

4.91 out of 5 average rating, 240 reviews

Townhouse in Ocean City

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.

Guest suite in Ocean City

4.98 out of 5 average rating, 366 reviews

The Elbridge Bayfront Studio

The Elbridge is a luxury studio apartment in downtown Ocean City. Beautiful bay view from studio windows. This bayside studio includes parking, a private garden entrance, and luxurious king bed. Located 4 blocks from the beach, the space is in a downtown residential neighborhood. Additionally included are bikes, bodyboards, beach chairs and a beach umbrella. Walking distance to delicious local restaurants, the boardwalk, and the beach!

4.9 out of 5 average rating, 40 reviews

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

Welcome to your modern and spacious 1-bedroom condo in Ocean City, Maryland! This centrally-located getaway is the perfect retreat for you and your loved ones, offering a comfortable and stylish space to enjoy your vacation. With enough room to accommodate up to 5 guests, this condo provides ample space for everyone to relax and unwind. Enjoy the bay views and a less than 5 minute walk to the beach and famous Ocean City boardwalk!

5 out of 5 average rating, 18 reviews

The Sunset House-Bayside-3 min drive to Beach

Welcome to The Sunset House, where the name says it all! This charming 1-bedroom, 1-bathroom retreat with a sleeper sofa is perfect for up to 4 guests. Recently updated, this waterfront oasis in the heart of Ocean City offers stunning water views and the added convenience of a private boat slip. The open floor plan maximizes space and natural light, with every detail thoughtfully renewed just last year for a modern, stylish stay.