Pineapple Bay ~ Private Pier + Sunsets

Entire townhouse in Ocean City, Maryland

  1. 10 guests
  2. 4 bedrooms
  3. 7 beds
  4. 3.5 baths
Hosted by Claudio
  1. Superhost
  2. 13 years hosting

Listing highlights

At-home gym

The stationary bike, yoga mat, and free weights are ready for workouts.

Self check-in

Check yourself in with the keypad.

Extra spacious

Guests love this home’s spaciousness for a comfortable 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.

The space
✦ 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.

Guest access
The townhouse is exclusively yours for the duration of your stay — no interruptions, no shared spaces. Simply arrive and make yourself at home.

Check-in is completely self-guided using a private key code — no need to coordinate with anyone or wait around. Your unique code will be provided prior to your arrival.
You'll have full access to everything the property has to offer:

✔ Entire Townhouse — All Levels
✔ Game Room
✔ All Outdoor Areas including the Deck & Both Balconies
✔ Private Pier (Fishing & Crab-Catching)
✔ EV Level 2 Charger
✔ 2 to 3 Dedicated Parking Spots & Free Street Parking

We know the area well — if you have any questions before or during your stay, we're always happy to help. Happy travels!

Other things to note
✦ DIGITAL GUIDEBOOK

Before arrival, you’ll receive access to our comprehensive mobile-friendly digital guidebook.

Inside you’ll find:

✔ Check-in instructions
✔ WiFi details
✔ House rules
✔ Property information
✔ Local dining, shopping & beaches
✔ Our favorite Ocean City recommendations

Everything you need — before and during your stay.

✦ NO SMOKING OR VAPING

Smoking and vaping are strictly prohibited inside and outside the home.

Any evidence will result in a minimum $875 fee to cover odor removal, duct cleaning, and furniture treatment.

✦ NO PARTIES

This property is for registered guests only.
Parties and unauthorized gatherings are not permitted.

✦ KAYAK & BICYCLES
Kayak and bicycles shown in photos are not available for guest use due to liability restrictions.

✦ NO PETS

Pets are not permitted at this property.

Registration Details
80511

Where you’ll sleep

1 of 2 pages

What this place offers

Shared beach access
Kitchen
Fast wifi – 53 Mbps
Dedicated workspace
Free parking garage on premises

Select check-in date

Add your travel dates for exact pricing

Rated 4.82 out of 5 from 73 reviews.

Guest favorite
This home is a guest favorite based on ratings, reviews, and reliability

Overall rating

  1. 5 stars, 90% of reviews
  2. 4 stars, 1% of reviews
  3. 3 stars, 8% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 4.6 out of 5 stars for cleanliness

Rated 4.8 out of 5 stars for accuracy

Rated 4.9 out of 5 stars for check-in

Rated 4.9 out of 5 stars for communication

Rated 4.8 out of 5 stars for location

Rated 4.8 out of 5 stars for value

Guest reviews mention

Where you’ll be

Ocean City, Maryland, United States
This listing's location is verified.

Neighborhood highlights

The home is at a beautiful waterfront location in the vibrant beach resort town of Ocean City, MD. Escape the everyday hustle and bustle of the big city and fill your lungs with healthy ocean air. The bayside townhouse is perfect for everyone who wants to avoid the hotel resort crowd and enjoy the serenity while being within walking distance of restaurants, shops, beaches, entertainment, and attractions.

Here are some places of interest you'll be looking to visit during your trip:

✔ Beach (4 min away)
✔ ACME Grocery (2 min away)
✔ Art League of Ocean City (2 min away)
✔ Coffee Beanery (2 min away)
✔ Blue Fish Restaurant (2 min away)
✔ Bull on the Beach (2 min away)
✔ Trattoria Lombardi's Pizza (2 min away)
✔ Liquid Assets Restaurant (3 min away)
✔ Bull on the Beach Restaurant (3 min away)
✔ Food Lion (4 min away)
✔ Hooked Restaurant (4 min away)
✔ Starbucks (5 min away)

Below are areas that are worth visiting:

✔ Jolly Roger Amusement Park (13 min away)
✔ Ocean City Boardwalk (14 min away)
✔ Ocean City Life-Saving Museum (15 min away)
✔ Rehoboth Beach (30 min away)
✔ Outlets (30 min away)
✔ Assateague Island National Seashore (30 min away)

***Distance times are calculated if traveling by car.

Meet your host

Superhost
420 reviews
4.8 out of 5 average rating
13 years of hosting
Born in the 70s
Where I went to school: University of Maryland
We’re Claudio and Lisa, and we love hosting guests at our homes in Berkeley Springs and Ocean City, MD. What started as a cabin renovation near Cacapon State Park became a passion for creating relaxing, well-appointed escapes. From peaceful forest retreats to bayfront oceanfront living with stunning, front-row sunset views in Ocean City, we focus on comfort, thoughtful details, and local recommendations to help you feel right at home. We look forward to hosting you.

Claudio is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.

Host details

Response rate: 100%
Responds within an hour
To help protect your payment, always use Airbnb to send money and communicate with hosts.

Things to know

Cancellation policy
House rules
Check-in after 4:00 PM
Checkout before 11:00 AM
10 guests maximum
Safety & property
Nearby lake, river, other body of water
Carbon monoxide alarm
Smoke alarm