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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
Sleeps 10•4 bedrooms•4 beds

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony
  • Free Wi-Fi

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

Rooms & beds

4 bedrooms (sleeps 10)

Basement Apartment Bedroom

1 King Bed

Bunk Bed

2 Single 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 # 2644650vb
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

About the area

Ocean City

Located in North Ocean City, a neighbourhood in Ocean City, this holiday 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 travelling 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 Holiday homes in Ocean CityOpens in a new window
Map
Ocean City, MD

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

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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

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
Response from VrboOwner on 9 Feb 2025
Thank you, Monica! We're so glad you had an amazing stay and enjoyed the space, cleanliness, and beautiful bay views. One of our favorite things about the property is the stunning sunset views from both the master bedroom balcony and the living room balcony—it’s the perfect way to unwind after a great day at the beach! We’d love to host you again for another relaxing getaway. Hope to see you soon!
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
Response from VrboOwner on 9 Feb 2025
Thank you, Christopher! We're so glad you enjoyed your stay and that you found the space clean, spacious, and relaxing. It was a pleasure hosting you, and we truly appreciate your kind words about our communication. We’re excited to share that we’ve made even more improvements for 2025, including a brand-new game room with life-size arcades, a ping pong table, and sports equipment for the nearby basketball, tennis and pickleball courts. Plus, we’ve upgraded the sofa bed and queen beds to luxurious king beds for even more comfort. We’d love to welcome you back to experience it all—hope to see you again soon!
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
Response from VrboOwner on 9 Feb 2025
Thank you so much for your kind words! We're thrilled to hear that you had a great stay and that everything met your expectations. Knowing you felt safe, comfortable, and enjoyed the location means a lot to us. We’re also happy you made the most of the space and amenities!
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
Response from VrboOwner on 9 Feb 2025
Thank you, Randall! We're so happy to hear that your first Ocean City vacation was a great one and that you enjoyed the location, views, and convenience of our place. It was a pleasure hosting you, and we appreciate your kind words about our communication. We’re also excited to share that we now have a new digital guide packed with information on the beach, shopping, dining, day trips, and much more to help make future stays even more seamless. We'd love to welcome you back anytime—hope to see you again soon!
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

Bob H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property for our first family vacation! Host was very responsive to our questions! Location was quiet but accessible to everything! Had everything we needed!
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Constance C.

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

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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