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. - ★Pineapple Bay★ ~ Private Pier + Sunsets (Ocean City)
A marina with boats docked, a wooden pier, and a building with balconies. - ★Pineapple Bay★ ~ Private Pier + Sunsets (Ocean City)
A modern kitchen with white cabinetry, stainless steel appliances, and a large island. - ★Pineapple Bay★ ~ Private Pier + Sunsets (Ocean City)
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and a dining area with a glass table and white chairs. - ★Pineapple Bay★ ~ Private Pier + Sunsets (Ocean City)
A waterfront property with a dock, a lifebuoy, and a building with balconies. - ★Pineapple Bay★ ~ Private Pier + Sunsets (Ocean City)
At ★Pineapple Bay★ ~ Private Pier + Sunsets, you can look forward to a playground, an arcade/games room and laundry facilities. Stay connected with free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as a gym.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 102400 sq ft

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.

    ✦ 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.

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
  • 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

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

Similar properties

Policies

Check-in

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

Check-out

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

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

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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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
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 cycling and ecotours. Visit our Ocean City travel guide
View more Holiday homes in Ocean City
Map
Ocean City, MD

What's nearby

  • A wooden pier extending into the ocean with a person standing at the end.
    Ocean City Beach
    18 min walk - 1.0 mile
  • A strip mall with various shops including NorMax, a sushi bar, and a pasta restaurant.
    Gold Coast Mall
    4 min drive - 1.8 miles
  • Assawoman Bay
    1 min walk - 0.1 miles
  • Art League of Ocean City
    11 min walk - 0.6 miles
  • 94th Street Ocean City Dog Playground
    14 min walk - 0.8 miles

Getting around

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

Restaurants

  • Dunkin'
    4 min drive
  • Bayside Skillet
    3 min drive
  • Reef 118
    4 min drive
  • Bamboo Lounge
    4 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 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. Maryland Beach is 2.2 mi (3.6 km) away.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

★Pineapple Bay★ ~ Private Pier + Sunsets Reviews