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★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 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 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

9.8 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.
  • Pickleball on-site
    A rare find — enjoy pickleball without leaving the property.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Ocean City Beach
4 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Balcony
  • Free WiFi

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

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.

✦ 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.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Bicycles and Kayaks in the Garage are not for Guest Usage
No Pets are allowed

Important information

You need to know

Property Registration Number 80511
Property # 2644650
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

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. The area's natural beauty can be seen at Ocean City Beach and Maryland Beach, while Jolly Roger Amusement Park and Frontier Town Water Park and Golf are popular area attractions. 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 ecotours.
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

  • ‪Wawa - ‬4 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Fager's Island - ‬6 min drive
  • ‪Denny's - ‬5 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 Aug 19, 2026, prices found for a 1-night stay for 2 adults at ★Pineapple Bay★ ~ Private Pier + Sunsets on Oct 26, 2026 start from $572, 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. Maryland Beach is 2.2 mi (3.6 km) away.

About the host

Hosted by Claudio Meira

Host profile image
We’re Claudio and Lisa, a married couple living in the Washington, D.C. area, and we truly love hosting guests at our bayfront townhouse in Ocean City.

Hospitality is important to us. We work hard to ensure your stay not only meets expectations — but exceeds them. From the moment you arrive, we want you to feel relaxed, comfortable, and at home, whether you’re enjoying coffee on the water or taking in the stunning corner-unit sunset views.

We’re always open to feedback and suggestions. Many of the features our guests love most came from past visitors’ ideas. If there’s anything that would make your stay even better, we genuinely want to hear from you.

We’re easy to reach and happy to help with recommendations, dining spots, beach tips, or anything you need during your stay.

We hope to welcome you soon!

Claudio & Lisa

Why they chose this property

We chose this neighborhood because it offers the perfect balance of peaceful bayfront living and unbeatable convenience. Located in a quieter area on the bay, it feels calm and relaxed — a welcome retreat after a busy beach day.

You’re less than a one-minute drive to the beach, restaurants, shops, mini golf, and local attractions. Even better, we offer two dedicated parking spots (and three depending on vehicle size), making family trips simple and stress-free — no hunting for parking during peak season.

In the evenings, you return to beautiful sunset views and a laid-back atmosphere away from the heavy crowds. For us, it’s the ideal mix of easy access, comfort, and coastal charm.

What makes this property unique

What makes our property unique is the rare combination of refined design, bayfront views, and resort-style amenities — all within minutes of the beach.

As a corner bayfront townhouse, the home is filled with natural light and open water views, creating an elevated and airy coastal atmosphere. The main living space blends sophisticated furnishings, light wood floors, and a seamless layout for gathering, dining, and entertaining in style.

All couple bedrooms feature king-size beds, offering true hotel-level comfort and space to unwind. Downstairs, the experience continues with a dedicated game room featuring full-size arcade machines and a premium ping pong table, along with a private exercise room for guests who like to stay active while away.

Step outside to your private bayfront deck and enjoy front-row sunset views — watch boats drift by and the sky transform over the water in total serenity.

Add dedicated parking, quick access to the beach, and a quieter bayfront setting, and you have a stay that feels more like a private waterfront retreat than a typical Ocean City rental.

Languages:

English, Spanish

Premier Host

They consistently provide great experiences for their guests
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