Holiday rentals with beach access in Ocean Pines

Guest suite in Ocean Pines

A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.

4.95 out of 5 average rating, 403 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

4.97 out of 5 average rating, 216 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Apartment in Ocean Pines

Ocean Pines Yacht Club Getaway Waterview

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

A cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.

4.87 out of 5 average rating, 101 reviews

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

A two-story blue house is framed by trees, with a well-maintained front yard. The home features black shutters and white steps leading to a central door. A porch flag and a welcoming bench are visible, enhancing the inviting exterior.

4.96 out of 5 average rating, 138 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

4.97 out of 5 average rating, 514 reviews

The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.

Townhouse in Ocean City

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Guest suite in Ocean Pines

A bright, open kitchen area is visible, featuring modern appliances and a spacious countertop. Large windows allow natural light to fill the room. A comfortable chair sits beside a decorative rug, while a sleek ceiling fan contributes to the airy atmosphere.

4.99 out of 5 average rating, 137 reviews

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.

4.94 out of 5 average rating, 322 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

4.98 out of 5 average rating, 102 reviews

The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.

Home in Berlin

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

A modern kitchen features light grey cabinetry and stainless steel appliances. A round table is set for dining, accompanied by stylish metal chairs. Natural light filters through the window, enhancing the warm, inviting layout that connects seamlessly to adjacent living spaces.

4.84 out of 5 average rating, 140 reviews

Peaceful Beach Cottage - Sanitized & WiFi!

Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*

A modern living area is presented, featuring a plush gray sofa and a minimalist coffee table. A large television is mounted on the wall opposite the seating. Natural light filters through sliding glass doors, which lead to a private balcony with a small table and chairs.

4.99 out of 5 average rating, 322 reviews

Steps to the Beach, Ocean View 1BR, Renovated

Steps to the beach! Fully renovated, bright, modern, clean condo with a balcony view of the ocean. Quiet North Ocean City location with walking distance to restaurants, bus, 7-11, Mini golf course, movie theater, parks, etc. Brand new appliances and furniture. Free WiFi, King Size Bed, 60" & 40" TVs. Pull Out Queen Sofa, Brand New Full Bathroom. Washer and Dryer in the unit. Keurig Coffee Station, iPhone Charging station. Private balcony. Free Parking Space.

An airy living space is highlighted by a high ceiling and large windows, inviting natural light. A gray sectional sofa faces a stone fireplace and a mounted television. Light blue cabinetry marks the kitchen area, with a dining table positioned nearby for flexibility.

5 out of 5 average rating, 15 reviews

Family Oasis - 4BR 3BA on Golf Course

TWO primary suites (4BR) and TWO living areas make this house double the fun! Our relaxed and beautiful home on a beautiful golf course is just 10 minutes from Ocean City. Enjoy all the amenities of Ocean Pines (pools, tennis courts, golf course, parks and walking trails). Parking for 6+ cars. House is loaded with well equipped spacious kitchen, great room with awesome entertainment setup, and tons of extra bedding options.

A modern living area features a light-colored sofa paired with two brown leather armchairs. A round wooden coffee table graces the floor, complemented by a textured area rug. Floor-to-ceiling glass doors provide unobstructed ocean views, while floor curtains add a pop of color.

4.92 out of 5 average rating, 153 reviews

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!

Popular amenities for rentals with beach access in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

5 out of 5 average rating, 24 reviews

Artsy Midtown OC Condo Ocean Block

The kitchen and dining area showcase a modern design with white cabinetry and stainless-steel appliances. A wooden dining table is surrounded by four white chairs. A cozy electric fireplace adds warmth to the space, which is illuminated by recessed lighting.

4.89 out of 5 average rating, 122 reviews

Rare Private Patio+Deck, Minutes Walk to OC Beach

Superhost

A spacious living area features a blue sectional sofa positioned in front of a wooden coffee table. A flat-screen TV is mounted on the wall, with two colorful landscape images above. In the background, a dining area is visible with high-top chairs and a kitchen countertop.

4.78 out of 5 average rating, 266 reviews

204 Bimini Large Direct Ocean Front Epic Views

A modern living area is presented with a gray sofa and a comfortable armchair. A coffee table sits beside the armchair, and a large artwork featuring a horse adorns the wall. Light-colored flooring complements the space, creating a bright and open atmosphere.

5 out of 5 average rating, 28 reviews

Luxurious Ocean Block condo

A bright living area showcases a large television mounted on a light-colored wall. A beige couch and cushions provide seating around a rectangular coffee table, which is adorned with decorative items. Floor-to-ceiling sliding glass doors offer unobstructed views of the ocean.

4.99 out of 5 average rating, 112 reviews

Stunning 3 Beds/2BA, Ocean Beachfront Condo

5 out of 5 average rating, 8 reviews

The "O.C. Crab House" on 32nd Street

A modern kitchen area is featured, with white cabinetry and a backsplash of stone tiles. A breakfast bar is recognized with high stools beside a wooden table. Natural light fills the space through a nearby door leading to a balcony.

4.92 out of 5 average rating, 37 reviews

Steps to sand and shops!

A balcony area is shown, featuring a round table accompanied by two lightweight chairs. A clear view of the ocean is visible, with a faint horizon line and soft clouds in the sky. The surrounding area includes a glimpse of the parking lot and buildings.

5 out of 5 average rating, 18 reviews

Ocean Paradise

House rentals with beach access

A welcoming living room features a cozy sofa and two armchairs arranged around a circular coffee table. A flat-screen TV is mounted above a fireplace, while a decorative area rug with floral patterns adds warmth to the space. Natural light streams through sheer curtains.

4.95 out of 5 average rating, 79 reviews

Cozy home in Ocean Pines

4.96 out of 5 average rating, 202 reviews

A charming bungalow features dark blue siding and large front windows, framed by neatly trimmed bushes. A concrete walkway leads to the front door, and a well-maintained lawn surrounds the home. The sky is partly cloudy, adding to the inviting exterior.

Home in Ocean City

Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!

A modern two-story home is situated on a tree-lined lot, featuring a welcoming front entrance. Brightly colored adirondack chairs provide seating in the gravel area by the driveway, which accommodates several vehicles. Natural light filters through the trees, creating a serene environment.

4.96 out of 5 average rating, 46 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

Superhost

A circular wooden deck overlooks tranquil waterfront views, featuring a mix of green grass and trees. Comfortable seating is positioned on the deck, allowing for relaxation while enjoying the serene surroundings. A two-story home and docks are visible in the background.

4.76 out of 5 average rating, 17 reviews

Oceans End Waterfront Retreat

4.98 out of 5 average rating, 66 reviews

Cozy home 8 miles from OCMD *Beach Pass Included*

A modern dining area features a rectangular table surrounded by six upholstered chairs. Large windows allow natural light to fill the space, with views of the surrounding trees. A stylish light fixture hangs above the table, and a door leads to the outdoor deck.

5 out of 5 average rating, 81 reviews

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

A spacious living area features a large gray sectional sofa, providing ample seating. A flat-screen TV is mounted on the wooden wall with a light-colored media console beneath. Natural light enters through sliding glass doors, complemented by curtains that frame the space against warm wooden ceilings.

5 out of 5 average rating, 9 reviews

Pines & Sea A-Frame • Coastal & Cozy Stay

4.95 out of 5 average rating, 102 reviews

A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.

Home in Ocean City

Spacious waterfront home & boat access!

Apartment rentals with beach access

The kitchen area features modern appliances and sleek cabinetry with a butcher block countertop. Two bar stools are positioned at the counter, creating a casual dining space. A cozy seating arrangement is nearby, complemented by a small table lamp and decorative elements.

4.89 out of 5 average rating, 107 reviews

Cozy beach side condo

The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.

5 out of 5 average rating, 111 reviews

Beautiful waterview 2B condo w/Dock&Close to Beach

A comfortably arranged living area features a light-colored sofa adorned with decorative pillows. A soft ottoman rests in front, and a wall-mounted artwork depicts a serene seascape. Natural light filters in through sheer curtains, while a modern lamp and a fan enhance the space.

4.99 out of 5 average rating, 105 reviews

Ocean block condo

A bright bedroom features a spacious bed with soft blue bedding and decorative pillows. Natural light floods in through two windows adorned with white trim, while a colorful wall art piece hangs above the bed. A side table with a basket adds functionality to the space.

4.97 out of 5 average rating, 201 reviews

The Search For Surf-Ocean Block Sleeps 4

A spacious living area is furnished with a comfortable sectional sofa and accent chairs, arranged around a wooden coffee table. Light wood accents and a large area rug complement the neutral tones of the room. Art pieces hang on the walls, adding visual interest.

4.98 out of 5 average rating, 117 reviews

Steps to Ocean! Beach Accessories. Uncrowded Beach

A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.

4.99 out of 5 average rating, 132 reviews

Gorgeous Beachfront! King Bed, Direct Ocean View!

An open-concept living area showcases a spacious sofa arranged around a light-colored coffee table, accented with decorative shells. A dining area with white bar stools and a fully equipped kitchen are visible in the background, along with coastal-themed decor and soft natural light.

4.98 out of 5 average rating, 112 reviews

Oceanside Charm, desirable midtown Ocean City, MD

The living room showcases a comfortable sofa facing a large television. A round coffee table sits in front, and a ceiling fan provides gentle airflow. Sliding glass doors open to a scenic waterfront view, allowing natural light to fill the space.