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About

On-Island. Operator-Led. Client-First.

Leeward Acquisitions is a property acquisition and management services firm. We believe clients deploying into Caribbean real estate deserve the same operational discipline, reporting transparency, and governance structure they expect from any professionally managed asset.

Sint Maarten on-island property and hospitality setting
Danielle Gaines, Principal of Leeward Acquisitions
Principal

Danielle Gaines

Danielle has spent the past fifteen years between Sint Maarten and Fort Lauderdale — building businesses, acquiring and managing properties, and developing the on-island relationships that make a service like Leeward Acquisitions possible.

Her background spans business operations, property management, and real estate acquisition across both the Dutch Caribbean and South Florida markets. She understands the regulatory environment, the vendor landscape, the seasonal dynamics, and the practical realities of owning property on a 34-square-mile island — because she lives there.

Danielle founded Leeward Acquisitions to bring operational discipline to a market that has historically been served by informal arrangements. She saw the gap firsthand: owners acquiring quality properties — often multiple units — with no reliable on-island partner to coordinate the acquisitions, set up the properties, and operate them as a unified portfolio after closing. The multi-property model is not a marketing concept. It is the specific problem this firm was built to solve.

She is the direct point of contact for every client. There is no sales team and no call center. When you engage with Leeward Acquisitions, you work with Danielle and the operations team she has built on-island over the past decade.

Philosophy

Our Approach to Clients

Direct Access, Not Layers

Every client has a direct line to a named principal. We don't scale by adding layers between you and the people making decisions. If you call, a person who knows your properties answers.

Alignment Before Agreement

We spend more time on engagement structuring than most operators spend on their entire intake process. If the fit isn't right — wrong timeline, wrong expectations, wrong market — we'll tell you. We'd rather decline an engagement than deliver a poor outcome.

Operate Like an Owner

Our reputation on-island is our only asset. Every property we manage reflects on us directly. We apply the same care and scrutiny we bring to our own holdings — because in a small market, your standards are your brand.

Transparency by Default

You see every invoice, every vendor charge, every line item. Expense approval thresholds are defined in your engagement — nothing surprises you. We believe opacity destroys trust faster than any mistake.

Protect the Downside

We focus on hurricane-resilient construction, adequate insurance, preventative maintenance, and conservative operating assumptions. Caribbean real estate rewards patience and punishes carelessness. We plan for storms — literally and figuratively.

Earn the Engagement

We onboard a limited number of new engagements per quarter to ensure each client receives dedicated attention during the critical first 90 days. Growth is deliberate, not aggressive.

Fee Structure

How We're Compensated

We believe clients should understand the cost structure before the first conversation, not after.

Acquisition Fee

A one-time fee based on the acquisition scope and complexity, defined in the engagement agreement before any sourcing begins. No hidden sourcing fees or undisclosed developer commissions.

Management Fee

An ongoing percentage of collected revenue for managed properties. The exact percentage depends on the rental strategy (short-term, mid-term, or long-term) and portfolio size. Full fee schedules are detailed in the Private Deck.

Setup & Furnishing

Costs are passed through at actual vendor pricing with full invoice transparency. Our coordination fee for setup scope is defined in advance.

No Performance Fees. No Hidden Charges.

We do not charge performance fees, disposition fees, or markup on vendor services. Our incentive is simple: well-managed properties that retain clients long-term.

Contact

Reach Us Directly

No forms required. Call, message, or email — whichever you prefer.

Sint Maarten (Dutch Side) · Fort Lauderdale, FL · Atlantic Time (AST / UTC-4)