
Holiday rentals near Jolly Roger at the Pier
We found 6,578 holiday rentals — enter your dates for availability
If you'd like to stay close to Jolly Roger at the Pier, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a pool. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Jolly Roger at the Pier
Showing deals for:14 Nov - 21 Nov
Image gallery for W. Fenwick Beach Retreat-Saltwater Pool and Canal Front! Minutes to Fenwick & OC

1010 out of 10 rating
Exceptional
(12 reviews)
W. Fenwick Beach Retreat-Saltwater Pool and Canal Front! Minutes to Fenwick & OC
Selbyville, DE
12% off
Price is £2,153
£2,153
£308 per night
includes taxes & fees
Image gallery for The 10th Tee Retreat - Luxury Bayside 5 Bedroom Home with Golf & Pond Views

1010 out of 10 rating
Exceptional
(5 reviews)
The 10th Tee Retreat - Luxury Bayside 5 Bedroom Home with Golf & Pond Views
Selbyville, DE
8% off
Price is £1,716
£1,716
£245 per night
includes taxes & fees
Image gallery for Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!

1010 out of 10 rating
Exceptional
(18 reviews)
Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
Ocean City, MD
7% off
Price is £1,869
£1,869
£267 per night
includes taxes & fees
Image gallery for Near it all OC beaches,Assateague island.Family-friendly white horse park

9.89.8 out of 10 rating
Exceptional
(38 reviews)
Near it all OC beaches,Assateague island.Family-friendly white horse park
Berlin, MD
7% off
Price is £781
£781
£112 per night
includes taxes & fees
Image gallery for Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

1010 out of 10 rating
Exceptional
(111 reviews)
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Berlin, MD
7% off
Price is £1,009
£1,009
£144 per night
includes taxes & fees
Image gallery for ★★★★★ Sleeps 6,Linens &Towels✓ Free Parking✓ Sunset View✓ Smart TVs✓ Pool ✓

1010 out of 10 rating
Exceptional
(65 reviews)
★★★★★ Sleeps 6,Linens &Towels✓ Free Parking✓ Sunset View✓ Smart TVs✓ Pool ✓
Ocean City, MD
11% off
Price is £795
£795
£114 per night
includes taxes & fees
Image gallery for Ready for 2025 summer in North Ocean City, Maryland!!!

1010 out of 10 rating
Exceptional
(21 reviews)
Ready for 2025 summer in North Ocean City, Maryland!!!
Ocean City, MD
11% off
Price is £1,090
£1,090
£156 per night
includes taxes & fees
Image gallery for Harbour Island Luxury Waterfront Condo Sunset View-Pool-Marina-Beach-Boardwalk

1010 out of 10 rating
Exceptional
(40 reviews)
Harbour Island Luxury Waterfront Condo Sunset View-Pool-Marina-Beach-Boardwalk
Ocean City, MD
8% off
Price is £2,530
£2,530
£361 per night
includes taxes & fees
Image gallery for Spacious Beach House for Family Vacation Rental

9.69.6 out of 10 rating
Exceptional
(31 reviews)
Spacious Beach House for Family Vacation Rental
Ocean City, MD
7% off
Price is £1,539
£1,539
£220 per night
includes taxes & fees
Image gallery for Perfect Sunsets-Direct Bay Front Condo! Crab and fish from the large deck.

9.89.8 out of 10 rating
Exceptional
(102 reviews)
Perfect Sunsets-Direct Bay Front Condo! Crab and fish from the large deck.
Ocean City, MD
18% off
Price is £1,001
£1,001
£143 per night
includes taxes & fees
Image gallery for Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!

9.69.6 out of 10 rating
Exceptional
(45 reviews)
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Ocean City, MD
7% off
Price is £4,192
£4,192
£599 per night
includes taxes & fees
Image gallery for True Ocean Front

8.88.8 out of 10 rating
Excellent
(29 reviews)
True Ocean Front
Ocean City, MD
7% off
Price is £4,133
£4,133
£590 per night
includes taxes & fees
Image gallery for Quiet Beachfront Retreat with Private Balcony

8.28.2 out of 10 rating
Very good
(25 reviews)
Quiet Beachfront Retreat with Private Balcony
Ocean City, MD
8% off
Price is £1,542
£1,542
£220 per night
includes taxes & fees
Image gallery for Waterfront Villa in Ocean City, Walking distance to the beach

9.29.2 out of 10 rating
Wonderful
(11 reviews)
Waterfront Villa in Ocean City, Walking distance to the beach
Ocean City, MD
7% off
Price is £1,325
£1,325
£189 per night
includes taxes & fees
Image gallery for Cozy Two bedroom/ two bath - short walk to the beach and Fenwick Island.

1010 out of 10 rating
Exceptional
(22 reviews)
Cozy Two bedroom/ two bath - short walk to the beach and Fenwick Island.
Ocean City, MD
7% off
Price is £1,109
£1,109
£158 per night
includes taxes & fees
Image gallery for GorgeousTownhouse,Beautiful Bay Views,1 block from Ocean, Free WiFi, linens inc.

1010 out of 10 rating
Exceptional
(116 reviews)
GorgeousTownhouse,Beautiful Bay Views,1 block from Ocean, Free WiFi, linens inc.
Ocean City, MD
8% off
Price is £2,236
£2,236
£319 per night
includes taxes & fees
Image gallery for 2BR 2BA condo parking, pool. Walk to beach, restau, minigolf waterpark, arcade

9.09.0 out of 10 rating
Wonderful
(19 reviews)
2BR 2BA condo parking, pool. Walk to beach, restau, minigolf waterpark, arcade
Ocean City, MD
7% off
Price is £680
£680
£97 per night
includes taxes & fees
Image gallery for Some Avail for 2025 Mid Town Ocean City on 69th St Townhome

9.69.6 out of 10 rating
Exceptional
(63 reviews)
Some Avail for 2025 Mid Town Ocean City on 69th St Townhome
Ocean City, MD
7% off
Price is £3,249
£3,249
£464 per night
includes taxes & fees
Image gallery for Spacious ocean front 1 bedroom condo sleeps 6, located in mid town Ocean City

1010 out of 10 rating
Exceptional
(17 reviews)
Spacious ocean front 1 bedroom condo sleeps 6, located in mid town Ocean City
Ocean City, MD
11% off
Price is £1,473
£1,473
£210 per night
includes taxes & fees
Image gallery for OC BEACH BLISS! OCEANVIEW BEAUTY STEPS TO BEACH! INDOOR POOL & ELEVATOR

9.89.8 out of 10 rating
Exceptional
(10 reviews)
OC BEACH BLISS! OCEANVIEW BEAUTY STEPS TO BEACH! INDOOR POOL & ELEVATOR
Ocean City, MD
7% off
Price is £1,079
£1,079
£154 per night
includes taxes & fees
Image gallery for Family friendly 3 Bedroom Condo only one block to the Beach!

9.49.4 out of 10 rating
Exceptional
(88 reviews)
Family friendly 3 Bedroom Condo only one block to the Beach!
Ocean City, MD
8% off
Price is £1,653
£1,653
£236 per night
includes taxes & fees
Image gallery for Oceanfront ~ 4 Seasons Balcony ~ Pool ~ Linens ~ Minutes To Boardwalk ~ 2025

1010 out of 10 rating
Exceptional
(175 reviews)
Oceanfront ~ 4 Seasons Balcony ~ Pool ~ Linens ~ Minutes To Boardwalk ~ 2025
Ocean City, MD
11% off
Price is £1,164
£1,164
£166 per night
includes taxes & fees
Image gallery for Oceanfront condo - sunrise views, direct beach access & pool

1010 out of 10 rating
Exceptional
(22 reviews)
Oceanfront condo - sunrise views, direct beach access & pool
Ocean City, MD
8% off
Price is £2,078
£2,078
£297 per night
includes taxes & fees
Image gallery for Beach Front with Amazing Views from Oceanside & Bayside

1010 out of 10 rating
Exceptional
(65 reviews)
Beach Front with Amazing Views from Oceanside & Bayside
Ocean City, MD
14% off
Price is £1,628
£1,628
£233 per night
includes taxes & fees
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Find properties near top attractions in Jolly Roger at the Pier
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Find the best place to stay - Jolly Roger at the Pier
Parrot Bay Townhouse 30 is a Classic Downtown Beach Getaway for the family looki
Sleeps 10 · 3 bedrooms · 2+ bathrooms
5.65.6 out of 10
4 reviews(4 reviews)
BREATHTAKING Ocean-Front Condo. Fully renovated. Outdoor Heated Pool
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Romantic Beach Getaway For 2 In Ocean City MD
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
Bayfront 2 bedroom condo with outdoor pool - perfect midtown location! Bay Princess #414
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Charming 3-bedroom house with AC and WiFi in pleasant Ocean City
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Alexander Mini Mansion in the Heart of Downtown OC
Sleeps 9 · 3 bedrooms · 3+ bathrooms
8.08.0 out of 10
Very goodvery good
7 reviews(7 reviews)
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
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- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value