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★Pineapple Bay★ ~ Private Pier + Sunsets

Family-friendly stay near Ocean City Beach

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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 modern kitchen with white cabinetry, stainless steel appliances, and a large island.
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and a dining area with a glass table and white chairs.
A waterfront property with a dock, a lifebuoy, and a building with balconies.
A marina with boats docked, a wooden pier, and a building with balconies.

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 10223 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Gym

Explore the area

View in a map
Ocean City, MD
  • Place, Assawoman Bay
    ‪1 min walk‬
  • Place, 94th Street Ocean City Dog Playground
    ‪14 min walk‬
  • Place, Ocean City Beach
    ‪18 min walk‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪55 min drive‬

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About the area

Ocean City

Seaside stay .Your stay at this North Ocean City vacation home places you within 3 miles (5 km) of Ocean City Beach and Maryland Beach. Assawoman Bay and Art League of Ocean City are also within half a mile (1 km).
View more Vacation homes in Ocean CityOpens in a new window

What's nearby

  • Assawoman Bay - 1 min walk - 0.1 km
  • 94th Street Ocean City Dog Playground - 14 min walk - 1.2 km
  • Ocean City Beach - 18 min walk - 1.5 km
  • Ocean City County Library - 19 min walk - 1.6 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

  • ‪Wawa - ‬4 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Crabcake Factory USA - ‬4 min drive
  • ‪Reef 118 - ‬4 min drive
  • ‪Bayside Skillet - ‬3 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

★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.

✦ CHEF-READY KITCHEN & DINING

Granite counters. Stainless appliances. Spacious island.

✔ Dining Table for 10
✔ Complete Cookware & Serveware

✦ Curated Coffee & Beverage Bar

✔ Breville Espresso Machine
✔ Keurig
✔ Drip Coffee Maker
✔ Ninja Smoothie System
✔ Complimentary Bag of Local Coffee

From handcrafted espresso to post-workout smoothies — your mornings are covered.

✦ CURATED WELCOME TOUCHES

✔ Complimentary locally roasted coffee
✔ Premium Nike or Under Armour tote — yours to keep

A small detail that makes a big difference.

✦ SLEEPING ARRANGEMENTS

Primary Suite — King Bed • Ensuite • Private Balcony

Bedroom 2 — Two Twin Bunk Beds

Bedroom 3 — King Bed

Bedroom 4 – Private Suite Level • King Bed • Ensuite • Balcony • Kitchenette • Fitness Area

✔ Echelon Bike
✔ StairMaster

Ideal for guests wanting privacy or a morning workout.

All bedrooms include Smart TVs and premium linens.

✦ GAME ROOM

✔ Full-Size Arcade Machines
✔ 3,000+ Game System
✔ Stiga Onyx Ping Pong
✔ Basketball & Sports Gear
✔ Beach Chairs, Carts & Umbrellas

Designed for family fun and competitive nights in.

✦ OUTDOOR EXPERIENCE

✔ Waterfront Main Deck with Dining
✔ Two Private Bedroom Balconies
✔ Private Pier for Fishing & Crabbing
✔ Spectacular Sunset Views

Few Ocean City rentals offer this level of private bay access.

✦ ADDITIONAL AMENITIES

✔ High-Speed WiFi
✔ Level 2 EV Charger
✔ Dual-Zone HVAC
✔ Washer & Dryer
✔ 2–3 Dedicated Parking Spots

Ideal for families, couples, and groups seeking upscale waterfront comfort just minutes from the beach.

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Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Kitchenette
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • 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
  • 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 elevator
  • Smooth flooring in public areas
  • Stair-free path to entrance
  • Well-lit path to entrance
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Double-glazed windows
  • Electric car charging station
  • Local artist showcase
  • Locally-owned and organized tours and activities
  • Some LED lighting used
  • Unit size: 2,400 square feet
  • Water dispenser

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

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

  • No pets 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property Registration Number 80511

Frequently asked questions

How close is ★Pineapple Bay★ ~ Private Pier + Sunsets to the airport?

This vacation home is 10 mi (20-min drive) away from the Ocean City, MD (OCE-Ocean City Municipal) airport, the closest popular airport to the property.

Does ★Pineapple Bay★ ~ Private Pier + Sunsets have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is ★Pineapple Bay★ ~ Private Pier + Sunsets to the beach?

This vacation home is 1.2 mi (3-min drive) from Ocean City Beach and 2.2 mi (8-min drive) from Maryland Beach. Don't forget your sunscreen!

Does ★Pineapple Bay★ ~ Private Pier + Sunsets offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at ★Pineapple Bay★ ~ Private Pier + Sunsets?

No, there is no casino at this vacation home, but Casino at Ocean Downs (16-min drive) is nearby.

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

Check-in begins at 4:00 PM.

Is there free parking at ★Pineapple Bay★ ~ Private Pier + Sunsets?

Free parking is not available at this vacation home.

Does ★Pineapple Bay★ ~ Private Pier + Sunsets have a pool?

This vacation home does not have a pool.

Does ★Pineapple Bay★ ~ Private Pier + Sunsets have a spa?

There are no spa services available at this vacation home.

How close is ★Pineapple Bay★ ~ Private Pier + Sunsets to downtown Ocean City?

This vacation home is 5.2 mi away from Ocean City.

★Pineapple Bay★ ~ Private Pier + Sunsets Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 9 out of 10 reviews
Rating 8 - Good. 1 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Michael M.

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

Sarah S.

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

Monica Z.

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
Verified review

10/10 Excellent

christopher m.

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
Verified review

10/10 Excellent

Tara B.

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
Verified review

10/10 Excellent

Randall S W.

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
Verified review

8/10 Good

Rachel K.

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

Stephen/Laura C.

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

Constance C.

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