Beach house holiday rentals in Ocean Pines

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!

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!

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

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.

Luxury Waterfront Condo-Sunset Views-Pool-Marina

Harbour Island is one of the most unique communities in all of Ocean City. Have lunch poolside as the world famous Reel Inn restaurant is connected to the pool area. A full service marina located within offers families the opportunity to observe local fisherman bringing in their daily catch! Tennis courts and a kiddie playground help to make this an unforgettable family stay! Our fully renovated home offers a large open kitchen, dining and living room views overlook the Isle of Wight bay.

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!

Beach Place North 2 | 4BR on Quiet Block

❗ Must be 25+ to rent and stay. No Senior Weekers, no pets, no smoking or vaping — no exceptions. Fines up to $1,000 if violated❗ ★★ Things to Know ★★ ✹ 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

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.

Oceanfront | Pool | Steps to beach | Elevator

Escape to a premier oceanfront studio with direct beach access! This unique building creates an experience reminiscent of being in a cruise ship stateroom. Perched on the 9th floor this unit offers endless views of the Atlantic ocean and sandy shores as far as you can see. Head to the beach and enjoy a multitude of activities: 🏊‍♂️ swimming 📚reading 🏄‍♂️surfing or paddle boarding 🏖️sunbathing 🪁 kite flying 🏐volleyball 🌊or simply relaxing to the sound of the waves

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.