Holiday Real Estate

What Holiday Real Estate does

Holiday Real Estate is a privately held, third-generation family-owned real estate company founded in 1969 and headquartered in Ocean City, Maryland. The company operates five physical offices across Ocean City and West Ocean City and delivers three integrated service lines: real estate sales (residential, vacation, and commercial property transactions in Ocean City, MD and Lower Sussex County, DE), vacation rentals (short-term weekly and nightly rental management for hundreds of properties), and long-term rentals (year-round and seasonal). Its customer base spans four primary segments: vacationers seeking short-term coastal accommodations, home buyers purchasing primary or vacation residences, property investors acquiring rental income assets, and retirees transitioning to coastal living.

The company's product surface is a multi-platform digital ecosystem layered on top of its physical office network. The two core products are a Rentals Platform at rentals.holidayoc.com (vacation and long-term rental search/booking) and a Sales Platform at sales.holidayoc.com (property search across Ocean City, Ocean Pines, Rehoboth Beach, Bethany Beach, Berlin, and the broader Eastern Shore / Coastal Delaware), supported by property management services and listing-onboarding flows for owners. Distribution is multi-channel: company-owned websites and call centers handle direct consumer sales and bookings, while Booking.com, Expedia, and VRBO distribute the rental inventory globally. The technology stack is not publicly documented and no AI/ML or proprietary platform features are disclosed.

Holiday Real Estate generates revenue from three streams: real estate sales commissions on completed transactions (transaction-fee model), management fees and rental income share on vacation rentals (managed-services model), and management fees on long-term rentals (managed-services model). Pricing is not publicly disclosed and varies by property. GTM is direct-to-consumer via five offices, call centers (800-638-2102 for rentals, 888-642-6251 for sales), and company websites, augmented by partner marketplace channels. Industry association partnerships (Maryland Realtors, VRMA, Coastal Realtors) and Ocean City Chamber of Commerce membership provide additional community visibility and professional credibility.

Name

Holiday Real Estate

Legal name

Holiday Real Estate, Inc.

Website

https://holidayoc.com

Company type

Private

Founded year

1969

Operating status

Operating

Headcount range

1–10 employees

Short description

Holiday Real Estate is a third-generation, family-owned real estate company founded in 1969 that operates five offices across Ocean City and West Ocean City, Maryland, providing residential and commercial property sales, vacation rental management, long-term rentals, and property management services to vacationers, home buyers, investors, and retirees.

Ownership category

akta.pro rank

Product category

Residential Real Estate Brokerage and Vacation Rental Management

SIC

Real Estate Agents & Managers (For Others) (6531)

akta.pro primary industry

Resort & Branded Residence Vacation Rental Management (BPAJAIAE)

akta.pro secondary industry

Beachfront & Lakefront Homes (THAMAAAF)

Keywords

• Vacation rental management
• Residential real estate sales
• Property management services
• Long-term rentals
• Coastal real estate brokerage

Headquarters

HQ city

Ocean City

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Infrastructure, Technology or R&D

Revenue model

1. Real Estate Sales: Full-service real estate sales including residential, vacation, and commercial property transactions in Ocean City, MD and Lower Sussex County, DE markets. Revenue generated through sales commissions on completed transactions.
2. Vacation Rentals: Management and rental of hundreds of vacation rental properties. Revenue derived from rental fees collected from vacationers, with property owners paying management fees for the service.
3. Long-term Rentals: Year-round and seasonal long-term rental property management services for property owners.

Go-to-market motion1 record

Distribution channels4 records

Marketing channels4 records

Core offering

Holiday Real Estate is a full-service coastal real estate company that brokers residential, vacation, and commercial property sales and manages hundreds of vacation and long-term rental properties in the Ocean City, Maryland and Lower Sussex County, Delaware markets. The company operates two core web platforms—one for rental searches and bookings and one for property sales—supported by five physical offices, on-staff real estate agents, and property management services for owners.

Product overview

Holiday Real Estate is a full-service real estate company operating as a multi-platform ecosystem consisting of two core products: a Rentals Platform (rentals.holidayoc.com) for vacation and long-term rental searches, and a Sales Platform (sales.holidayoc.com) for property purchases. These are complemented by Property Management services for owners, and two listing services for property owners to list either for sale or for rent. The company has been in business for over 55 years, serving the Ocean City, MD and Lower Sussex County, DE markets.

Differentiator

Problem solved

Functional benefit

Products and services

• Vacation and Long-Term Rentals Platform
• Real Estate Sales Platform
• Property Management Services Rental property management services for property owners, covering maintenance, tenant coordination, and rental listing management across the company's portfolio of hundreds of vacation and long-term rental properties.
• List Your Property (Sales) Service allowing property owners to list their residential, vacation, or commercial properties for sale with Holiday Real Estate's licensed sales agents.
• List Your Property (Rentals) Service allowing property owners to list their properties for rent with Holiday Real Estate's rental management team, gaining access to the company's direct booking platform and OTA distribution network.

Quantifiable outcome

• Customer reviews indicate rapid response times with maintenance issues addressed within 1 hour in at least one documented case
• +1 more outcomes

Named customers7 records

Segments4 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

Seven partnerships are on record, tiered minor and core.

• Coastal RealtorsminorChannel Partner/ Reseller/ DistributorListed as a partner organization, likely representing referral or networking relationship within the real estate industry.
• Booking.comcoreChannel Partner/ Reseller/ DistributorMajor vacation rental distribution partner listing Holiday Real Estate properties on the Booking.com platform for global vacation rental market access.
• Maryland RealtorsminorChannel Partner/ Reseller/ DistributorState-level real estate association partnership providing industry networking and professional development resources.
• ExpediacoreChannel Partner/ Reseller/ DistributorVacation rental distribution partner listing properties on Expedia's travel platform, expanding reach to Expedia's extensive traveler base.
• Ocean City Chamber of CommerceminorGTM or Marketing PartnerLocal business community partnership supporting regional tourism and business development initiatives in the Ocean City area.
• VRMA (Vacation Rental Management Association)minorChannel Partner/ Reseller/ DistributorIndustry association membership representing professional vacation rental management companies with standard-setting and networking benefits.
• VRBOcoreChannel Partner/ Reseller/ DistributorHomeAway/VRBO platform partnership distributing vacation rental listings to the vrbo.com marketplace and Expedia's vacation rental network.

Scale indicators5 records

Recent moves5 records

Expansion highlights3 records

Direct peers

• TurnKey Vacation Rentals: Tech-enabled vacation rental management company focused on whole-home coastal properties. Overlaps directly with Holiday Real Estate's beachfront vacation rental portfolio across multiple US destinations.
• Vacasa: Largest US full-service vacation rental management company. Directly comparable to Holiday Real Estate's vacation rental management business, operating at far greater scale with proprietary technology and dynamic pricing.
• Evolve Vacation Rental: National vacation rental manager with a lighter-touch, partner-driven model. Comparable to Holiday Real Estate on the rental management side, though operates at national scale with no real estate brokerage arm.

Broad incumbents

• Century 21: Global real estate franchise with strong presence in Mid-Atlantic beach and resort communities. Comparable to Holiday Real Estate's sales business, particularly in second-home and vacation property transactions.
• Coldwell Banker: Global residential real estate franchise with strong Mid-Atlantic and coastal presence. Comparable to Holiday Real Estate's real estate sales business, though offers vacation rental only through affiliates rather than in-house.
• Coldwell Banker Vacations: Vacation rental arm of Coldwell Banker operating in resort markets. Comparable to Holiday Real Estate's combination of real estate sales and vacation rental management in a coastal resort context.
• Berkshire Hathaway HomeServices: National real estate brokerage franchise network with coastal resort market presence. Comparable to Holiday Real Estate on the residential and vacation property sales side, though operates as a national umbrella brand rather than a localized operator.
• RE/MAX: International residential real estate franchise with significant coastal resort market share. Comparable on the brokerage and residential sales side, operating a franchise model versus Holiday Real Estate's direct local ownership.

Regional players

• Long & Foster Real Estate: Dominant Mid-Atlantic residential real estate brokerage with significant Delaware and Maryland beach market share. Closely comparable regional peer for Holiday Real Estate's sales operations in Ocean City and Lower Sussex County.
• Vantage Vacation Rentals: Regional Ocean City, MD vacation rental management company. Direct geographic competitor to Holiday Real Estate's vacation rental business, focused on the same Ocean City and Eastern Shore submarket.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• Xx.com/ocmdrentals

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Holiday Real Estate