Beach house holiday rentals in Ocean Pines

New! Oceanfront at Marigot Beach

This exquisite oceanfront condo at Marigot Beach offers the ultimate coastal living experience in the heart of Ocean City, MD. Enjoy breathtaking sunrises and panoramic views of the sparkling Atlantic from your private balcony. With its modern design, spacious layout, and upscale amenities, this luxurious retreat is perfect for relaxing getaways. Experience the beach lifestyle at its finest with direct access to the sand, proximity to local attractions, and a vibrant seaside community! Book Now

Relaxing Montego Bay/Fishing/2 Pools/Corner house

You will be welcomed by a large living room, dining room, and kitchen combination. 4 bedrooms all with cable TV and wifi, 2 sleeper sofas, and 2 bathrooms. Sit on the deck and enjoy the sun or eat crabs outside at picnic table. Great amenities 2 pools, walking blocks to the Ocean, walk along the bay, enjoy fishing, and the kids friendly park. Rent bicycles in the boardwalk early in the morning. Relax with the family at this wonderful place to stay. Linen can be purchased, or bring your own.

2 BR Ocean Front Condo w/Pool, Expansive Views

Your family will be close to everything when you stay at this beautiful condo located right on the beach with expansive balcony views of both ocean and bay. With the best amenities around, this year-round rental is equipped with an enormous indoor pool, basketball and tennis courts, shuffleboard, saunas, gym, library, sun deck, & game room with arcades, claw machines, billiards, and air hockey tables. This 2-bedroom unit comfortably sleeps 6 which makes it ideal for families or couples alike.

NEW!OceanView-Pool-Sundeck-Bike-Theater-Game Room

Welcome to Your Elegant Oceanview Escape Home Experience the perfect blend of upscale comfort and family-friendly amenities in this spacious 5-bedroom retreat designed to host unforgettable getaways. Overlooking the sparkling coastline, steps from the beach, this home sleeps 16+ and offers everything you need to relax, recharge, and reconnect. Highlights • Breathtaking ocean views from multiple decks • Pool and sundeck (Pool closes Sept 29th 2025) • Arcade/game room • Outdoor movie deck!

Direct Oceanfront Penthouse

Come vacation at this direct oceanfront penthouse on 85th Street! This 3 bedroom, 3 bath two-story penthouse offers plenty of space for the entire group to stretch out and enjoy. Expansive bay and ocean views, the oversized balcony is the place you will want to be! The building offers a heated pool and is only a few small steps to the beach. For your convenience, this unit has a washer and dryer inside the property. In addition, games, beach chairs, and beach toys are available for your use!

Ocean, Beach, Boardwalk, and Fun

Newly renovated throughout in 2025 with the Beach 😎 just 150 steps away and the quiet end of the boardwalk is a block away. Your family or friends will enjoy easy access to everything from this centrally located place. Whether it’s the beach, the boardwalk, or all the amenities you would need they are within a few steps. Plus you have a reserved parking spot!! And additional free street parking nearby If you are bringing the kids, Jolly Roger amusement park is right across the street..

Robin Hood Retreat

Explore the Eastern Shore from this beautiful Ocean Pines home with 4 King Bdrms, 3 1/2 baths. Bring the whole family for a couple's week to enjoy the local sights. Full Kitchen, DR, LR, FR, Sunroom, Deck & Patio on a quiet residential street. Berlin, the OC Boardwalk & Assateague Island are minutes away for a fun filled day. Amenity filled The Ocean Pines Community with pools, golf, tennis and food & live entertainment. Must be 25 or prior service military or first responder to rent.

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

“The Pelican’s Perch”

Spacious one bedroom condo with a great ocean view. Best ocean view in the building! Nice balcony to enjoy coffee & watch the waves & pelicans fly by. The building has an indoor pool and family game room. Large outdoor lounge area with picnic tables & view. Walking distance to north side park, great restaurants and entertainment. Beach is obviously right there to enjoy and parking is on location in private lot under cover. Dogs are permitted but only from Oct 1 thru April, off season