Beach house holiday rentals in Ocean Pines

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+old

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..

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

Ocean-front getaway, amazing views, dog friendly!

Perfect getaway to the ocean in this updated, stylish home. Elevated ocean-front, with stunning views from every room and two private balconies. Amazing location - walk to great restaurants and still enjoy a private-feeling beach with lifeguard stand just steps away. No need to 'pack' for the beach -the house is just steps away. Enjoy coffee at the granite island overlooking the beach! There is a set of stairs up to the condo, and another set of stairs up to the main bedroom.

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 Include: • Breathtaking ocean views from multiple decks • Pool and sundeck • Arcade/game room • Outdoor movie deck

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, crabbing and the kids friendly park. Rent bicycles in the boardwalk early in the morning. Relax with the whole family at this wonderful place to stay.

Oceanfront | Steps to beach | Pool | Elevator

Enjoy this premier oceanfront location with convenient access to the beach. This unique building creates an experience reminiscent of being on a cruise ship balcony. Perched on the 9th floor, the unit offers endless views of the Atlantic Ocean and the beach. Just steps away from the sand, you can spend your days swimming, reading, sunbathing, surfing, paddle boarding, kiting, playing volleyball, or simply listening to the crashing waves.