Holiday rentals near Jolly Roger at the Pier
We found 6,598 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:31 Oct - 7 Nov
Image gallery for Fabulous Fenwick Island Waterfront property!
1010 out of 10 rating
Exceptional
(201 reviews)
Fabulous Fenwick Island Waterfront property!
Selbyville, DE
8% off
Price is AU$3,938
AU$3,938
AU$563 per night
includes taxes & fees
Image gallery for 5BR OceanView O/D Space/Movies, Pool, Bikes, Gear
9.69.6 out of 10 rating
Exceptional
(28 reviews)
5BR OceanView O/D Space/Movies, Pool, Bikes, Gear
Ocean City, Maryland
7% off
Price is AU$6,811
AU$6,811
AU$973 per night
includes taxes & fees
Image gallery for Relax at Bay Breeze, a fully equipped 3BR oasis, just a mile to amazing beaches!
1010 out of 10 rating
Exceptional
(5 reviews)
Relax at Bay Breeze, a fully equipped 3BR oasis, just a mile to amazing beaches!
Selbyville, DE
8% off
Price is AU$2,396
AU$2,396
AU$342 per night
includes taxes & fees
Image gallery for Modern Waterfront Home w Pool, Yard, Dock, Kayaking, King Beds, Amazing!
1010 out of 10 rating
Exceptional
(37 reviews)
Modern Waterfront Home w Pool, Yard, Dock, Kayaking, King Beds, Amazing!
Selbyville, DE
8% off
Price is AU$4,730
AU$4,730
AU$676 per night
includes taxes & fees
Image gallery for Oceanfront 2 bed/ 2 full bath condo with ocean & bay views. Lots of ammenities!
9.49.4 out of 10 rating
Exceptional
(67 reviews)
Oceanfront 2 bed/ 2 full bath condo with ocean & bay views. Lots of ammenities!
Ocean City, MD
8% off
Price is AU$5,430
AU$5,430
AU$776 per night
includes taxes & fees
Image gallery for Bayside Resort - 5 Bdrm/3.5 Bath w Backyard Pond - Pools Kayaks Beach Golf
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Bayside Resort - 5 Bdrm/3.5 Bath w Backyard Pond - Pools Kayaks Beach Golf
Selbyville, DE
8% off
Price is AU$4,026
AU$4,026
AU$575 per night
includes taxes & fees
Image gallery for Relax Here in this quiet Beach house!
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Relax Here in this quiet Beach house!
Ocean City, MD
8% off
Price is AU$2,583
AU$2,583
AU$369 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
(63 reviews)
★★★★★ Sleeps 6,Linens &Towels✓ Free Parking✓ Sunset View✓ Smart TVs✓ Pool ✓
Ocean City, MD
6% off
Price is AU$1,732
AU$1,732
AU$247 per night
includes taxes & fees
Image gallery for Oceanfront nestled in the dunes
1010 out of 10 rating
Exceptional
(23 reviews)
Oceanfront nestled in the dunes
Ocean City, MD
7% off
Price is AU$2,960
AU$2,960
AU$423 per night
includes taxes & fees
Image gallery for The Plaza - Direct Oceanfront Luxury Condo with Beach bar-Discount weekly
9.29.2 out of 10 rating
Wonderful
(81 reviews)
The Plaza - Direct Oceanfront Luxury Condo with Beach bar-Discount weekly
Ocean City, MD
8% off
Price is AU$3,093
AU$3,093
AU$442 per night
includes taxes & fees
Image gallery for 4 Bed W/ Pool Steps to the Beach/Ride
9.69.6 out of 10 rating
Exceptional
(11 reviews)
4 Bed W/ Pool Steps to the Beach/Ride
Ocean City, MD
12% off
Price is AU$7,746
AU$7,746
AU$1,107 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
(44 reviews)
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Ocean City, MD
7% off
Price is AU$8,361
AU$8,361
AU$1,194 per night
includes taxes & fees
Image gallery for Oceanfront ~ 4 Seasons Balcony ~ Pool ~ Linens ~ Minutes To Boardwalk ~ 2025
1010 out of 10 rating
Exceptional
(173 reviews)
Oceanfront ~ 4 Seasons Balcony ~ Pool ~ Linens ~ Minutes To Boardwalk ~ 2025
Ocean City, MD
8% off
Price is AU$3,004
AU$3,004
AU$429 per night
includes taxes & fees
Image gallery for NEW Condo private outdoor space, 1.5 blocks to our FREE beach and POOL too!
9.29.2 out of 10 rating
Wonderful
(35 reviews)
NEW Condo private outdoor space, 1.5 blocks to our FREE beach and POOL too!
Ocean City, MD
7% off
Price is AU$2,587
AU$2,587
AU$370 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
(114 reviews)
GorgeousTownhouse,Beautiful Bay Views,1 block from Ocean, Free WiFi, linens inc.
Ocean City, MD
8% off
Price is AU$4,590
AU$4,590
AU$656 per night
includes taxes & fees
Image gallery for Newly Renovated Condo- mins from Seacreats/ Convention Center & Jolly Rodgers
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Newly Renovated Condo- mins from Seacreats/ Convention Center & Jolly Rodgers
Ocean City, MD
7% off
Price is AU$1,343
AU$1,343
AU$192 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
(62 reviews)
Some Avail for 2025 Mid Town Ocean City on 69th St Townhome
Ocean City, MD
8% off
Price is AU$6,544
AU$6,544
AU$935 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 AU$3,232
AU$3,232
AU$462 per night
includes taxes & fees
Image gallery for Beautiful ground floor remodeled condo steps to the beach
1010 out of 10 rating
Exceptional
(19 reviews)
Beautiful ground floor remodeled condo steps to the beach
Ocean City, MD
8% off
Price is AU$4,978
AU$4,978
AU$711 per night
includes taxes & fees
Image gallery for Waterfront Villa in Ocean City, Walking distance to the beach
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Waterfront Villa in Ocean City, Walking distance to the beach
Ocean City, MD
8% off
Price is AU$2,676
AU$2,676
AU$382 per night
includes taxes & fees
Image gallery for The Sandpiper: Beautiful Ocean Block Family-Only Rental 3 Bed 2 Bath W/ Parking!
9.89.8 out of 10 rating
Exceptional
(54 reviews)
The Sandpiper: Beautiful Ocean Block Family-Only Rental 3 Bed 2 Bath W/ Parking!
Ocean City, MD
23% off
Price is AU$2,494
AU$2,494
AU$356 per night
includes taxes & fees
Image gallery for Spacious Ocean View Condo
8.88.8 out of 10 rating
Excellent
(93 reviews)
Spacious Ocean View Condo
Ocean City, MD
5% off
Price is AU$2,192
AU$2,192
AU$313 per night
includes taxes & fees
Image gallery for Beautiful Downtown Property - Steps to the Boardwalk & Beach!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Beautiful Downtown Property - Steps to the Boardwalk & Beach!
Ocean City, MD
7% off
Price is AU$9,019
AU$9,019
AU$1,288 per night
includes taxes & fees
Image gallery for Relaxing Breezy Seaside Retreat Oceanfront, Boardwalk 3bd 2ba 2decks King Bed
1010 out of 10 rating
Exceptional
(28 reviews)
Relaxing Breezy Seaside Retreat Oceanfront, Boardwalk 3bd 2ba 2decks King Bed
Ocean City, MD
9% off
Price is AU$6,680
AU$6,680
AU$954 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
Romantic Beach Getaway For 2 In Ocean City MD
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
Parrot Bay Townhouse 30 is a Classic Downtown Beach Getaway for the family looki
Sleeps 10 · 3 bedrooms · 2+ bathrooms
5.45.4 out of 10
3 reviews(3 reviews)
Charming 3-bedroom house with AC and WiFi in pleasant Ocean City
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
BREATHTAKING Ocean-Front Condo. Fully renovated. Outdoor Heated Pool
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
67 reviews(67 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
6 reviews(6 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)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
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All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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