Entire home

★Pineapple Bay★ ~ Private Pier + Sunsets

Photo gallery for ★Pineapple Bay★ ~ Private Pier + Sunsets

A living room with a sofa, a coffee table, and a chair. There is a balcony with a view of the water and buildings.
A waterfront property with a dock, a lifebuoy, and a building with balconies.
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and a dining area with a glass table and white chairs.
A modern kitchen with white cabinetry, stainless steel appliances, and a large island.
A marina with boats docked, a wooden pier, and a building with balconies.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Ocean City Beach

Popular amenities

  • Balcony
  • Kitchenette
  • Toys
  • On-site fitness center
  • Electric vehicle charging point
  • Air conditioning

Explore the area

View in a map
Ocean City, MD
  • Place, Assawoman Bay
    ‪1 min walk‬
  • Place, Ocean City Beach
    ‪18 min walk‬
  • Place, Gold Coast Mall
    ‪4 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪55 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Basement Apartment Bedroom

1 King Bed

Bunk Bed

2 Twin Bunk Beds

Master Bedroom

1 King Bed

Secondary Bedroom

1 King Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 4

Soap · Towels provided · Toilet · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Separate dining area
Outdoor play area
Dining area

Add dates for prices

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About the neighborhood

Ocean City

Located in North Ocean City, a neighborhood in Ocean City, this vacation home is near theme parks and on the waterfront. Jolly Roger Amusement Park is a popular attraction and the area's natural beauty can be seen at Ocean City Beach and Maryland Beach. Consider Seacrets for a night out or Carousel Ice Skating Rink if you're traveling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and horse riding.
View more Vacation Homes in Ocean CityOpens in a new window
Map
Ocean City, MD

What's nearby

  • Assawoman Bay - 1 min walk - 0.1 km
  • Art League of Ocean City - 11 min walk - 1.0 km
  • 94th Street Ocean City Dog Playground - 14 min walk - 1.2 km
  • Ocean City Beach - 18 min walk - 1.5 km
  • Gold Coast Mall - 4 min drive - 2.8 km

Getting around

  • Ocean City Station - 14 min drive
  • Ocean City, MD (OCE-Ocean City Municipal) - 20 min drive

Restaurants

  • ‪Dunkin' - ‬4 min drive
  • ‪Bamboo Lounge - ‬4 min drive
  • ‪Bayside Skillet - ‬3 min drive
  • ‪Ropewalk Ocean City - ‬3 min drive
  • ‪Crabcake Factory USA - ‬4 min drive

Frequently asked questions

Is ★Pineapple Bay★ ~ Private Pier + Sunsets pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at ★Pineapple Bay★ ~ Private Pier + Sunsets?

As of Nov 6, 2026, prices found for a 1-night stay for 2 adults at ★Pineapple Bay★ ~ Private Pier + Sunsets on Nov 9, 2026 start from $507, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at ★Pineapple Bay★ ~ Private Pier + Sunsets?

Check-in begins at 4:00 PM.

What time is check-out at ★Pineapple Bay★ ~ Private Pier + Sunsets?

Check-out is at 11:00 AM.

Where is ★Pineapple Bay★ ~ Private Pier + Sunsets located?

This family-friendly Ocean City vacation home is located on the waterfront, within 1 mi (2 km) of Assawoman Bay and Ocean City Beach. Art League of Ocean City and 94th Street Ocean City Dog Playground are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 10 out of 11 reviews
Rating 8 - Good. 1 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall great experience! Highly recommend!
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
loved the place lots to do around the area. hosts were great
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just as pretty and spacious as it looks in the pictures!
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

We had such an amazing stay at this property. Beautiful home, very clean and spacious! Great location and gorgeous views of the bay!
Stayed 3 nights in Jun 2022
Response from VrboOwner on Feb 9, 2025
Thank you, Monica! We're so glad you had an amazing stay and enjoyed the space, cleanliness, and beautiful bay views. One of our favorite things about the property is the stunning sunset views from both the master bedroom balcony and the living room balcony—it’s the perfect way to unwind after a great day at the beach! We’d love to host you again for another relaxing getaway. Hope to see you soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place with awesome view!

Place was very spacious and clean. Nice big deck for relaxing and watching the bay. Everything was new and updated. Owners were very nice and had great communication for anything you need. Definitely gonna stay here again!
Stayed 4 nights in Jun 2023
Response from VrboOwner on Feb 9, 2025
Thank you, Christopher! We're so glad you enjoyed your stay and that you found the space clean, spacious, and relaxing. It was a pleasure hosting you, and we truly appreciate your kind words about our communication. We’re excited to share that we’ve made even more improvements for 2025, including a brand-new game room with life-size arcades, a ping pong table, and sports equipment for the nearby basketball, tennis and pickleball courts. Plus, we’ve upgraded the sofa bed and queen beds to luxurious king beds for even more comfort. We’d love to welcome you back to experience it all—hope to see you again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Experience!

We had a great stay. The pictures were exactly like the unit. We felt safe and was in a great location to the main strip. The balconies and space in each bedroom were excellent as well. Many items were provided and helped to provide a comforting stay as well as everything was rather clean. We had a blast!
Stayed 3 nights in Jul 2022
Response from VrboOwner on Feb 9, 2025
Thank you so much for your kind words! We're thrilled to hear that you had a great stay and that everything met your expectations. Knowing you felt safe, comfortable, and enjoyed the location means a lot to us. We’re also happy you made the most of the space and amenities!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Property on the Bay

This was my first time vacationing at Ocean City and this property was great! Very close to numerous great restaurants, grocery stores, and beach access areas. The communication was quick and easy with the owner. Everything was as advertised on the property listing. The views from the deck overlooking the bay are awesome! It is an easy 15-20 minute to the parking for the boardwalk. We’ll definitely stay here again!
Stayed 3 nights in Jul 2022
Response from VrboOwner on Feb 9, 2025
Thank you, Randall! We're so happy to hear that your first Ocean City vacation was a great one and that you enjoyed the location, views, and convenience of our place. It was a pleasure hosting you, and we appreciate your kind words about our communication. We’re also excited to share that we now have a new digital guide packed with information on the beach, shopping, dining, day trips, and much more to help make future stays even more seamless. We'd love to welcome you back anytime—hope to see you again soon!
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Long weekend with Family

We arrived on a Sunday and while there were a few issues the hosts resolved them quickly. The house is huge with a great eating area, a nice deck overlooking the water and a huge kitchen table. The bedding was super comfortable and the bed linens were high quality. The upper floor of the house gets very hot during the day but we were able to cool it down in time for sleep. The water pressure in the master bathroom is low but was a minor inconvenience. Overall we were happy with our stay. The location was fantastic.
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Plus

The home was as advertised. The pictures dont lie. Beautiful bay views from large living room and master bath. It just worked out bery well for our family of 7 (and comfortably grew to 9 for one night). The absolute PLUSES were things like:- The gameroom was a home run. Without spending an extra dime, our family spent a solid two hours playing the the many commercial-grade video games and a fully functional ping pong table. We stayed in and it was like going out...but better.- Our group included a three-year old and the Harry Potter themes 9 3/4 Hogwarts was amazing. All the adults were happy to crawl under the stairs with our little one, and enter a pretty authentic Harry Potter space.- My son was able to "go crabbing" and even catching a few crabs with his daughter. A first-time, cool experience. This could happen because not only does the proper have a very nice and safe dock, the owners left a few clean and ready-to-go crab pots. Picked up some chicken, dopped the pot in the water by the dock and next morning, two crabs. Good memory. The place was amazing and NOT as advertised...it was better.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property for our first family vacation! Host was very responsive to our questions! Location was quiet but accessible to everything! Had everything we needed!
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Jul 2024
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