★Pineapple Bay★ ~ Private Pier + Sunsets

Ocean City, Maryland
$607 avg/night Minimum Stay 3 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 3 nights

Min Stay

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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Double-glazed Windows Energy-saving Switches Local Artist Showcase Locally-owned & Organized Tours & Activities Unit Size: 2400 Sq Ft (223 Sq M) Uses Some LED Lighting
  • KITCHEN

    Blender Dishwasher Electric Kettle Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Electric Car Charging Station On Site Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Outdoor Furniture
  • BATHROOMS

    3.5 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    2 Outdoor Pickleball Courts Basketball Nearby Ecotours Nearby Fitness Center Fitness Facilities Nearby Golf Privileges Kayaking Nearby Marina Nearby Parasailing Nearby Sailing Nearby Surfing/body Boarding Nearby Tennis On Site Theme Parks Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Games Music Library Table Tennis Video Games Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Playground
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping Near The Bay Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Limited Housekeeping
  • 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 Elevators Smoke-free Property Smooth Flooring In Public Areas Stair-free Path To Entrance Well-lit Path To Entrance

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Sarah S.

    Submitted Aug 15, 2025

    Stayed Aug 10, 2025

    Just as pretty and spacious as it looks in the pictures!

  • Rachel K.

    Submitted Jul 23, 2025

    Stayed Jul 6, 2025

    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.

  • Stephen/Laura C.

    Submitted Jun 30, 2025

    Stayed Jun 23, 2025

    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.

  • Michael M.

    Submitted Jun 16, 2025

    Stayed Jun 13, 2025

    loved the place lots to do around the area. hosts were great

  • christopher m.

    Submitted Jun 15, 2023

    Stayed Jun 10, 2023

    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!

  • Tara B.

    Submitted Aug 1, 2022

    Stayed Jul 28, 2022

    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!

  • Randall S W.

    Submitted Jul 20, 2022

    Stayed Jul 17, 2022

    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!

  • Monica Z.

    Submitted Jul 7, 2022

    Stayed Jun 23, 2022

    We had such an amazing stay at this property. Beautiful home, very clean and spacious! Great location and gorgeous views of the bay!

Your dates are Available!

Total

Includes taxes and fees
$607+
View details