Beach house holiday rentals in Maryland Beach

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+older

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 & reconnect. Highlights • Breathtaking ocean views from multiple decks • Pool and sundeck Pool Opens 05-23 to Sept 28th 2026 • Arcade/game room • Outdoor movie deck

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.

Oceanfront Penthouse - Ocean & Bay Views with Pool

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!

Shell House A

Seize this rare beachfront opportunity to rent a fully custom remodeled unit, offering a total of 3 bedrooms, 3 bathrooms, and a heated outdoor shower. This modern and luxurious units boast privacy while being centrally located, just steps away from the beach for easy access to sun and surf. The unit has been meticulously designed with high-end finishes and attention to detail. Includes dual balconies, all the amenities and covered parking for added convenience for a wonderful family vacation

Sunlit Surf Haven • Entire Home Steps to Beach

Welcome to Sunlit Surf Haven! A newly renovated entire home (2024) - ocean-block in Midtown Ocean City. Ride the coastal vibe in this bright surf-inspired retreat that sleeps 6 with two large beds and bunk beds. Enjoy on-site parking (2 spots) plus street parking, and beach gear included - chairs, umbrella, cooler, and blankets - for effortless beach days. Walk to shops, mini golf, and favorites like The Bonfire, Hooked, Bayside Skillet, OCM Crabs, and Ropewalk - just steps from the sand.

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.

The Blue Crush - 3BR Beachfront Family Retreat

Experience the magic of coastal living at 'The Blue Crush'. It's COMPLETELY REMODELED including 3 bedrooms and a deck to watch the sunrise over the ocean and sunset over the bay. If your family is looking for more space. Our sister beach house, Orange Crush is located next door, has 5 bedrooms and can accommodate up to 12 guests. Combining your stay at the Orange and Blue Crush, you accommodate up to 20 guests, in 8 bedrooms. Please reach out to us for special group pricing.

Closest condo to the beach in OC! 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.

Boardwalk Oasis Incredible Views, Pets Bikes

This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED This 3 bed/2 bath BOARDWALK & OCEANFRONT cottage is your perfect beach escape in Ocean City! Just steps from the sand, this property has all the essentials with some exciting extras to boost! House bikes all included! Relax in comfort after a day of seaside fun. Whether you're strolling the boardwalk or enjoying ocean views, this cottage has it all!

OCEAN FRONT! 4BD/10Beds/3FullBaths, Ocean Colony

Oceanfront Beach House! Great Mid-town location; Seacrets Bar, Restaurant & Night Club is across the street. Beach vibes through out house; great room opens to beachfront deck; 3 sundecks; fully stocked kitchen. 4 bedrooms & loft, total of 10 beds: hear waves crash from the master bedroom; "Surfer's Lounge" w/oceanfront deck. Wi-Fi & Cable; Garage. Private Sand Beach for Grilling & Volley Ball. Linens and towels provided. Check us out!

Beach Place North 2 | 4BR on Quiet Block

★★ Things to Know ★★ ✹ Must be 25+ to rent and stay - no graduating HS groups. ✹ Parking: Carport parking for up to 2 vehicles (size dependent) ✹ Outdoor community pool available seasonally ★★ Things to Love ★★ ✹ Direct beach access with multiple private decks and ocean views ✹ Enjoy one of the least crowded stretches of beach — NO nearby high-rises ✹ Private backyard space, rare for Ocean City beachfront homes