Beach house holiday rentals in Ocean Pines

Relaxing Breezy Seaside 3bd/2ba/2decks King Bed

Wake up to stunning ocean views and the soothing sound of waves at this charming beachfront home. Relax on the breezy indoor and outdoor living decks. Enjoy recently updated stainless steel appliances, quartz countertops, and a fully tiled walk-in shower. The primary bedroom has direct access to the oceanfront deck, with ocean views in every bedroom. Nearby: Jolly Roger Amusement Park Boat Tours & Fishing Jetski & Parasailing Need more space? Rent the sister house next door! Message for details.

TwoBlockstoBeach&Boardwalk! Pool! PingPong! Bikes!

Modern and sophisticated Ocean City beach retreat, two blocks from the boardwalk and beach -Luxury 3 Bedroom, 3.5 bathroom condo -Completely Updated -85 inch TV with Soundbar -Full Kitchen, well stocked, air fryer etc. -Coffee bar with Keurig Duo, French Press, Pour Over, and grinder -3 private balconies -Community Pool -Garage with full sized ping pong table and cornhole -Four new Huffy Cruiser bikes -10 backpack beach chairs -King, Queen, Full Size, and Bunk Beds with full sofa bed-sleeps 10

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

Family Townhouse, Rooftop Jacuzzi, Walk to Beach

Escape to Ocean City, MD, and indulge in the ultimate beachside luxury at our two-bedroom retreat. Just steps from the sandy shores, this modern haven features a rooftop jacuzzi, walk to the beach, and an EV charger. Enjoy breathtaking ocean views from the rooftop deck, complete with lounge furniture for unforgettable evenings under the stars. Inside, every room boasts state-of-the-art amenities, ensuring your comfort. Book your seaside escape now and experience coastal living at its finest!

Beautiful Cottage W/ shared pool & close 2 beach

"Beautifully decorated & completely renovated 3 BR/2 BA/ plus den. The home is 2 blocks from the bay and a 20 min. walk to the beach! Enjoy this entire home in the quiet neighborhood of Montego Bay which boasts 2 pools, tennis courts, a fishing pier, a walking pond, mini golf and Northside Park. The kitchen is fully stocked and the house is kid-friendly. There are 2 parking spaces & off-street parking. Finally, enjoy the sunset on the large deck complete with an area for al fresco dining.

Direct Ocean Front - Beach Retreat Condo!

Wake up to amazing sunrises and the sound of the waves from this beautiful Ocean front condo with spectacular views! Recently remodeled with new custom walk-in shower!! Large PRIVATE balcony overlooks the heated pool and beach. Perfect to catch a view of the dolphins or relax after a day at the beach or pool! The light & airy open kitchen has views of the ocean and is well-equipped with new granite countertops, new stainless appliances. Ocean views from the living room & dining area!

OC MD trip bayside, great amenities

Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC/beaches & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stay

Snug Harbor Hideaway

Escape to Snug Harbor Hideaway, a 4-bedroom, 2-bath bayfront and canalfront retreat located in Berlin, MD. This cozy bungalow offers stunning water views from every angle, a peaceful front porch for your morning coffee, and a spacious backyard perfect for family dinners under the sky. Bring along a small boat and dock right at the bulkhead for effortless adventures. Enjoy a 10 min drive to Assateague Island and Ocean City’s beaches, restaurants, and nightlife!