Holiday rentals in Isle of Wight Bay

4.97 out of 5 average rating, 158 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!

4.97 out of 5 average rating, 166 reviews

Apartment 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, 167 reviews

Luxury Oceanfront Escape!

This unique place has a style of its own. Wake up, pour your cup of coffee, and watch the sunrise from your direct oceanfront balcony. The beach is a few short steps away. Walking distance to many restaurants and shops! This recently renovated one bedroom condo features an outdoor shower, an elevator, fully equipped kitchen, a library of books, 1.5 bathrooms, Wi-Fi, large screen smart tv, bedroom tv, parking spot, washer/dryer and so much more! Fresh linens, towels, and toiletries 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!

4.92 out of 5 average rating, 809 reviews

Light and Airy Oceanfront Condo with Large Porch

Wake up to the sound of the waves crashing outside your window and finish off your days relaxing on the private balcony as you watch the moon rise over the ocean. Come find your serenity by the sea in our modern oceanfront condo. Located in midtown Ocean City, you can keep your car parked in our dedicated spot and walk to many of the towns best restaurants, bars, and entertainment as well as the Convention Center and Performing Arts Center. Morning beach strolls and evening sips await :)

4.99 out of 5 average rating, 95 reviews

The Hideaway By The Bay OCMD

Relax and enjoy your stay in this bright and welcoming waterfront, 1 bed, 1 bath condo. Bring your kayaks or paddle boards! This condo is located right off of 28th street, on the bay. It is a 14 minute walk to the beach and the Ocean City boardwalk, and within walking distance to many Ocean City attractions. All guests are provided with an electronic WELCOME BOOK prior to arrival which includes everything we think they will need to know about the condo and the surrounding area.

Superhost

4.85 out of 5 average rating, 202 reviews

Beachfront 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 a breathtaking 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, 363 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!

4.89 out of 5 average rating, 221 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!

4.98 out of 5 average rating, 281 reviews

Tiny home in Selbyville

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

4.9 out of 5 average rating, 132 reviews

Ocean Side Condo-Steps From The Beach!

Enjoy a relaxing getaway at our Ocean Side condo. Just steps from the beach, our condo is centrally located on 44th St. Within walking distance of the Convention Center, Seacrets, 44th St. Taphouse, Mini Golf, and many other restaurants and shopping. Fully furnished, updated, clean, and modern. Washer/Dryer in unit.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Isle of Wight Bay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Isle of Wight Bay

4.95 out of 5 average rating, 19 reviews

Flat in Ocean City

Studio Condo Steps to the Beach

RyanRating, 5 stars5 days ago

Rhonda was a very friendly & attentive host & she was very helpful our whole stay! The whole place was very clean & conveniently located, perfect stay & highly recommend!

Flat in Ocean City

4.77 out of 5 average rating, 30 reviews

62nd St, Ocean City, Direct walk to beach w pool

EneaRating, 5 stars1 month ago

great place for a quick getaway! great host A+++

4.94 out of 5 average rating, 33 reviews

Home in Ocean City

Cheerful home with bay and skyline views.

JuliannaRating, 5 stars1 month ago

This was my second stay here, and I’ll definitely be back again! The host is consistently friendly, responsive, and easy to communicate with. Check-in and check-out are super easy, which makes the whole experience smooth and stress-free. The house is cozy, clean, and located in a quiet neighborhood with a beautiful view. It’s far enough from the main part of Ocean City to feel peaceful, but just 3 minutes from all the action when you want it. There are tons of great restaurants nearby, and the host has excellent recommendations. A perfect spot for a comfortable and relaxing stay!

5 out of 5 average rating, 5 reviews

Flat in Ocean City

Bayside Breeze! 6 Guests, 2 bedrooms: 1 bathroom

RebeccaRating, 5 stars1 day ago

Not only was the apartment, beautiful and clean. Val was very accommodating and helpful our entire stay. She was easy to reach, and any questions we had she answered right away. The amenities inside the apartment were great to have available as well. Overall, it was a great stay, and I would definitely recommend this place!

4.78 out of 5 average rating, 106 reviews

Jolly Rogers is steps away (condo)

GillianRating, 5 stars2 weeks ago

I will be back again! We had a wonderful getaway. The balcony is where to be. We enjoyed it and I know if you are just looking for some peace and quiet you will too! Just 10min walk from the beach but a 10min drive to the boardwalk. You can see sunsets from the balcony.

4.98 out of 5 average rating, 40 reviews

Oceanfront 1 Bdrm-Sleeps 4-Linens-Pool-WiFi

JamesRating, 5 stars2 weeks ago

Beautiful space with a view thats worth the price and more. I wanted to get some writing done and this was the perfect spot. Jack was very proactive and helpful. The space is flawlessly layed out for a private retreat/solo getaway/or small family. One minor issue that really isnt on the host ... the parking people tried to charge me $20 per day for parking until I showed my confirmation. The lady was still very nice and honored the one-time $40 fee but just be sure to let them know before you pay I guess. Nonetheless, amazing experience and will def be back next time I visit OC.