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About Us

Our Story

Kaystreet Management was born from a simple observation: the short-term rental industry was missing a truly professional asset management approach.

 

As hospitality professionals ourselves, we saw firsthand how traditional property managers were failing to maximize the potential of short-term rentals. They either treated them like hotels without the necessary systems and data analytics, or like long-term rentals without understanding the unique operational demands of the STR market.

We founded Kaystreet in 2025 with a vision to bring institutional-quality management to the short-term rental space—combining sophisticated revenue optimization with meticulous operational execution. We believe that whether you own one property or one hundred, you deserve a management partner who treats your investment with the same care and strategic thinking as a large-scale asset manager.

 
Our mission is to transform the fragmented STR management industry by building a company that delivers consistently superior results through systems, data, and a relentless focus on both guest experience and owner returns. We’re not just managing properties—we’re building the next generation of hospitality asset management.

Methodology

The Kaystreet method

Revenue
Science

We treat pricing as a science, not an art. Through continuous market analysis, competitive benchmarking, and demand forecasting, we optimize your property's pricing in real-time to capture maximum value from every booking opportunity.

Operational Excellence

We believe exceptional guest experiences come from systematic processes, not random efforts. Our detailed operational playbooks ensure consistent, high-quality execution across every guest touchpoint and property maintenance task.

Technology Integration

By seamlessly connecting best-in-class platforms with custom automations, we create an operating system that scales efficiently while maintaining personalized service. This tech foundation enables both operational precision and data-driven decision making.

Market Positioning

We strategically position each property to target the most profitable guest segments. Through optimized listings, targeted marketing, and amenity curation, we attract guests willing to pay premium rates for quality experiences.

Continous Optimization

We never stop improving. Through rigorous performance tracking and A/B testing, we continuously refine our approach to drive incremental gains in both guest satisfaction and financial returns.

Leadership

Our Leadership team

Jake Goodman

Jake Goodman is the founder of Kaystreet Management and a seasoned hospitality professional with deep experience across both short-term rentals and hotel investment. Before launching Kaystreet, Jake successfully built and scaled a short term rental management company, gaining firsthand knowledge of what it takes to grow profitable STR portfolios through strategic marketing, efficient operations, and data-backed revenue management.

After exiting his initial venture, Jake transitioned into hotel brokerage, where he worked on over $100 million in hotel dispositions and underwrote more than $1 billion in hotel assets for both private owners and institutional investors. His rare combination of operational expertise and investment-level financial analysis allows him to approach short term rental management with an owner’s mindset and a sharp eye on long-term value.

With Kaystreet, Jake brings the same professionalism and performance standards trusted by hotel investors to the world of short term rental management.

VALUES

Our Core values

Ownership Mindset

We manage every property as if it were our own investment. This means making decisions that prioritize long-term asset value and sustainable returns, not just short-term convenience.

Data Driven Excellence

We believe in the power of data to drive better decisions. From pricing to operations, we measure, analyze, and optimize based on real performance metrics, not assumptions or industry conventions.

We're Built on Transparency

We provide complete visibility into your property's performance and our management activities. You'll always know exactly how your investment is performing and what we're doing to improve results.

Systematic Execution

We don't rely on individual heroics or ad-hoc solutions. Instead, we develop robust systems and processes that ensure consistent, high-quality execution across all properties and guest interactions.

Growth Partnership

We measure our success by your success. Whether that means maximizing returns on a single property or helping you build a portfolio, we're committed to being a true partner in achieving your investment goals.

CLIENT

Testimonials

Kaystreet Management has completely transformed the performance of my property. Their dynamic pricing and strategic marketing have significantly increased my booking rate and revenue. The team’s dedication and responsiveness make them an invaluable partner in managing my property.
Shaya GoldsteinProperty Owner in Tampa, FL
I was struggling with guest communication and operational inefficiencies until I started working with Kaystreet Management. Their streamlined processes and excellent customer service have not only improved guest satisfaction but also reduced vacancy rates. I’m seeing a consistent boost in revenue, and I couldn’t be more pleased.
Emma HansenProperty Owner in Clearwater Beach, Fl
Working with Kaystreet Management has been a game changer for my portfolio. They took the time to understand my goals and provided a tailored strategy for each of my properties. Their team’s focus on continuous optimization has resulted in noticeable revenue growth and operational efficiency across all my units.
David KaufmanProperty Owner in St. Pete, FL