Nestled in a tranquil Ocean City neighborhood, this 4 bedroom, 3.5 bath townhouse offers a peaceful escape with the perfect blend of quietude and accessibility. Enjoy sunsets from the spacious outdoor deck and balcony or indulge in your favorite activities like ping pong and arcade games in the game room.
Reviews
9.89.8 out of 10
Exceptional
Entire home
4 bedrooms4 bathroomsSleeps 10223 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Gym
Add dates for prices
About this property
★Pineapple Bay★ ~ Private Pier + Sunsets
Luxury 4BR bayfront townhouse in Ocean City, MD. Enjoy stunning sunsets from the private deck, fish or catch Maryland blue crabs from your private pier, and unwind in beautifully designed spaces. King beds for every couple, custom bunks for kids, plus a full arcade game room, premium ping pong, fitness room, and hidden Harry Potter room. Just minutes from the beach in a private bayside location. Your unforgettable waterfront escape awaits.
✦ SUMMER 2026 UPGRADE
All beds upgraded to premium King-size mattresses. Now featuring 3 King beds + 2 bunk beds — spacious comfort for more guests.
We continually invest in Pineapple Bay to elevate your stay.
✦ NO LINENS FEE
Beds are professionally made before arrival. Premium linens and plush towels included. No extra charges. No setup required.
✦ MAIN LIVING SPACE
Open-concept and filled with natural light.
✔ Large L-Shaped Sectional ✔ 75” Smart TV ✔ Surround Sound System ✔ Direct Access to Waterfront Deck
Watch boats pass by as the sky turns gold at sunset.
Ideal for families, couples, and groups seeking upscale waterfront comfort just minutes from the beach.
Property amenities
Beach
Beach nearby
Beach loungers
Beach towels
Internet
Available in the house: Free WiFi
Parking and transport
Electric car charging station on site
Parking on site
Kitchen
Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Kitchen island
Kitchenette
Lobster/crab pot
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster
Water dispenser
Dining
Dining table
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3.5 bathrooms
Bathtub or shower
Hair dryer
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Living room
Separate dining area
Entertainment
Books
Games
Music library
Smart TV with cable/satellite channels
Video games
Video library
Outdoor areas
Balcony
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
No lift
Smooth flooring in public areas
Stair-free path to entrance
Well-lit path to entrance
Smoke-free property
Services and conveniences
Iron/ironing board
Limited housekeeping
Location highlights
Near a health/beauty spa
Near a hospital
Near an outlet shopping centre
Near the bay
Near the marina
Near the sea
On the waterfront
Things to do
2 outdoor pickleball courts
Arcade/game room
Gym
Optional golf privileges
Table tennis
Tennis
Basketball nearby
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Horseback riding nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Surfing/bodyboarding nearby
Swimming nearby
Theme park nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Bicycles and Kayaks in the Garage are not for Guest Usage
No Pets are allowed
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number 80511
We should mention
This property does not have any lifts
About the area
Located in North Ocean City, a neighbourhood in Ocean City, this holiday 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 travelling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and ecotours. Visit our Ocean City travel guide
Is ★Pineapple Bay★ ~ Private Pier + Sunsets pet-friendly?
No, pets are not allowed at this property.
How much is parking at ★Pineapple Bay★ ~ Private Pier + Sunsets?
On-site 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?
Checkout is at 11:00 AM.
Where is ★Pineapple Bay★ ~ Private Pier + Sunsets located?
This family-friendly Ocean City holiday 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.
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★Pineapple Bay★ ~ Private Pier + Sunsets Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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!
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.
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!
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!
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.