
Places to stay near Jolly Roger at the Pier
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Top-rated holiday rentals near Jolly Roger at the Pier
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Gorgeous Beachfront! King Bed, Direct Ocean View!
Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

Dolores by the Sea- Family Groups ONLY
This recently remodeled 1950's house is walking distance to the beach, boardwalk, & fabulous restaurants. Tucked away from the hustle & bustle in a quiet neighborhood this cozy home is the perfect place to relax after a fun filled day at the beach. This home has 4 bedrooms & up to 7 beds. With a wheelchair ramp & a fenced in yard this house is perfect for family gatherings & making memories. Please note that due to neighborhood restrictions we cannot book to unrelated renters under 27 years old

Downtown Condo, Parking, Walk to Beach & Boardwalk
Modern 2BR/2BA downtown Ocean City condo with bay view, balcony, elevator, pool, and parking. Sleeps 6 with 1 king and 2 queen beds. Walk about 1,000 ft to the inlet beach, boardwalk, rides, pier, dining, festivals, and downtown events. Enjoy a full kitchen, dishwasher, washer/dryer, smart TVs, WiFi, linens, bath towels, beach towels, chairs, umbrella, and cooler. Includes 1 assigned parking space plus 1 shared first-come space with passes. Perfect for families, couples & event-goers year-round.

Assateague Views! Top Floor -Assateague House #505
Welcome to your perfect getaway at Assateague House, a beautifully appointed 2-bedroom, 2-bathroom condo with breathtaking southerly views of Assateague Island and a Bay Front Pool! This serene and spacious retreat is just steps from the Ocean City boardwalk, offering the best of both worlds—relaxing coastal scenery and easy access to shops, dining, and entertainment. ***Linens Not Included (Bedsheets, Pillowcases, Beach,Bath, Dish Towels) ***Linens can be arranged through a local linen company.

Edgewater Escape - Luxury Bayfront Loft with Porch
You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Downtown-Pool-Boardwalk-Bay Views-Marina-Boat Slip
Luxury waterfront condo conveniently located two blocks from the world famous attractions on the Ocean City boardwalk. A short walk will have you sitting on the beach in minutes. Afterwards, take a dip in the community pool. Be sure to watch for the charter boats as they bring in their daily catch to the marina below. Enjoy happy hour on your private balcony overlooking beautiful bay sunset views. Whatever you're looking to do, our unit is perfectly situated in the heart of it all!

3BR Belmont Towers on Boardwalk ,Ocean & Bay Views
Enjoy PANORAMIC OCEAN & BAY VIEWS in one of Ocean City's NEWEST Buildings-Belmont Towers directly on BOARDWALK! Unbeatable location! ALL LINENS INCLUDED AND IN PLACE 24/7 Fast Customer Service Highlights Include: *huge balconies w/ direct access from living room & bedroom *outdoor pool *putting green *fitness center *washer/dryer *smart TVs in each bedroom *jetted tub in master bathroom *steps to Jolly Roger, Thrashers & many other restaurants *2 Free garage parking spaces

Sunkissed Ocean Haven
Welcome to Sunkissed Ocean Haven, a stunning 3-bedroom, 3-bath beachfront retreat in Ocean City, MD! Fully renovated in 2023, this luxurious unit features en-suite bathrooms for all bedrooms, a spacious kitchen, and a wet bar. Enjoy panoramic ocean views from the primary bedroom and living room, breathtaking sunsets, and direct beach access. With a pool, sauna, fitness center, and parking garage, plus top restaurants and nightlife nearby, this prime location offers it all!

Bright and Airy Oceanside Condo
Wake up to stunning ocean sunrises from your private balcony and enjoy bay sunsets just outside your front door. This oceanside condo in midtown Ocean City, MD is steps from the beach!! Beachside with no street to cross. Park your car for free in our covered lot. Enjoy a walkable location near top restaurants, bars, nightlife, and attractions like Seacrets, Fager’s Island, Macky’s, breakfast at barn 34 and mini golf. Ideal for a convenient Ocean City beach vacation.

Fabulous Boardwalk Oceanfront w/ Pool
Beautiful 3 bedroom, 3 bathroom, 3rd floor oceanfront condo on the Ocean City Boardwalk! This unit sleeps up to 11 guests and offers free Wi-Fi, HDTVs, large balcony that overlooks the boardwalk, gourmet kitchen, beach chairs and umbrella in locker. New 75" Samsung TV in Living room, *Linens are not provided, but can be added to your reservation for a fee **NO RENTALS TO ANY GROUPS UNDER THE AGE OF 25** Families with children are welcome! *No Smoking, No Pets*

Riptide Beach House
This three-bedroom retreat is full of charm and excitement. Step inside and be delighted. The first bedroom offers a comfortable double bed, perfect for a restful night. The second bedroom features a spacious king bed. In the third bedroom, you'll find two cozy double beds, ideal for sharing good times and relaxation. With everything you need to unwind and create lasting memories, your perfect getaway is right here. Let’s have some unforgettable moments together!

Gated Renovated 2 Level Condo Downtown OC Bayview
Welcome to a Newly Renovated Two level condo in downtown Ocean City. Sunny 2 bedroom 2 bath with views of sunsets over the bay from a private balcony. Comes fully furnished and kitchen stocked with tons of gadgets. Smart TV’s in every bedroom and living area with Disney plus, YouTube tv, and Netflix. Feel Secure with gated building and parking. No car needed as restaurants, activities, boardwalk, jet ski rentals all within 2 blocks.
Popular amenities for holiday rentals near Jolly Roger at the Pier
Condo rentals with Wi-Fi

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Perfect location!

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Bayside Retreat in the Heart of Ocean City!

Beach Paradise 202-Downtown Luxury Condo Bay View

The Sea Voyage Canal Front 1 Bedroom Condo

Cozy beach side condo

Oceanfront Family Oasis: Pool, Beach & Parking!
Family-friendly house rentals

Assateague, Golf, Ocean City, all Within Minutes!

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Sleeps 19 - 7br/4ba/2 kitchens Entire Home

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Sweet Retreat

Camelot

Charming Waterfront Cottage w/2 King Suites + Dock

SpaciousCondo nearOcean City|Winery|Golf on 5Acres
Apartment rentals with air conditioning

Coastal 2 Bedroom Apartment w/pool

Oceanside Condo Steps From Beach

Handful of Beach Heaven!

Lovely 2 bedroom overlooking Main St.

Fresh renovated beach home~12 street

Amazing oceanfront view 3 blocks from boardwalk

Studio Charm w/ Deck: Walk to Beach & Dining!

West Ocean City: Private Studio, Close To Beach
Other great holiday rentals near Jolly Roger at the Pier

Boardwalk Serenity: Oceanfront Penthouse Sleeps 12

Heart of Downtown OC. 5 Car Garage.1 Blk to Ocean

Lovely apartment in the heart of downtown

Oceanside in Bethany Dunes, Steps to Private Beach

BeachBox IV • Walk to Boardwalk • Bayside Pool

Steps to OC boardwalk with partial bay views

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

PENTHOUSE - 8TH Floor Boardwalk/Epic Views/Pool/
Destinations to explore
- Chincoteague Island
- Cape May Beach NJ
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Ocean City Beach
- Broadkill Beach
- Rehoboth Beach
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Assateague State Park
- Willow Creek Winery & Farm
- Northside Park
- Wildwood Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Mariner's Arcade
- Funland
- Ocean City Boardwalk
- Hawk Haven Vineyard & Winery
- Bear Trap Dunes





