Buy Businesses in Monroe County, FL | Florida Keys Listings

Searching for Monroe County, Florida businesses for sale? DealStream offers an exclusive selection of prime Florida Keys business listings—from Key West waterfront restaurants and Key Largo marinas to luxury vacation rentals in Marathon and boutique shops in Islamorada. Each opportunity includes detailed financials and direct seller contact, making it easy to evaluate and acquire your ideal enterprise. Browse now and start your entrepreneurial journey in the vibrant Florida Keys!

All Matching Deals

South Florida Tax Practice. 400 Plus Loyal Clients
Monroe County, FL

South Florida Accounting & Tax Practice for Sale: Well-established practice operated by an accountant and assistant, ideal for an owner-operator or as an add-on acquisition for a larger firm seeking additional clients and recurring revenue. The practice prepares approximately 370 personal returns (1040s)...

$75,000
Cash Flow: $48,000
Details
Build Your Way To Profit
Monroe County, FL

One of the most established and trusted names in residential and commercial construction is ready for new owners to take it into its next era of profitability! Serving the Florida Keys and beyond with year-over-year growth, this general contracting business has remained profitable and virtually recession-proof...

$500,000
Cash Flow: $166,858
Details
Monroe County, FL

This established boutique offers a curated selection of apparel, fabrics, accessories, and home-lifestyle goods in one of Key West’s highest-traffic retail corridors. The store benefits from exceptional year-round visibility, a strong tourist customer base, and a loyal following among repeat local clients....

$150,000
Cash Flow: $86,631
Details
Profitable Bait & Tackle Shop | Islamorada, FL
Monroe County, FL

Bait & Tackle Shop – Islamorada Established in 2019, this profitable shop serves local anglers and tourists with live and frozen bait, premium tackle brands (NLBN, Nomad, Johnny Jigs), and is an authorized Penn dealer. The store also offers fishing apparel, snacks, drinks, beer, seltzers, and wine...

$515,000
Cash Flow: $143,514
Details
Monroe County, FL

It’s time to be your own boss! Work-life balance, financial success, & the rewarding experience of helping customers transform their vessels into something they absolutely love can be yours with this custom marine decking Biz. Exceptional financial performance. Gross margins of 50-65% & Net in the...

$615,000
Cash Flow: $237,744
Details
Marathon, Florida, Practice for Sale
Marathon, FL

Established acupuncture practice collecting $64,831.00 [3-av]. $40k in equipment/furnishings. Current owner has had to turn away new patients & treatments due to a restricted schedule. Marathon is an affluent resort community in the heart of the Florida Keys. Practice has a healthy ratio [mix] of locals...

On Request
Details
Key West, FL

Awesome fun business next to the beach with real estate in Key West with seller financing,Henna Tattoos, body jewelry, Hair Wrap and Hair Extensions, Fashion Hair Braids. Has very large margin on products can be anywhere from 60% up to 80% you will have all the support and training you need from the...

$1,975,000
Details

Tips for Buying A Business In Monroe County, FL

Research the Local Market

Monroe County, which covers the Florida Keys, has a unique economy heavily influenced by tourism, hospitality, and seasonal fluctuations. Begin your search by thoroughly researching the local market trends, predominant industries, and customer demographics. Take note of factors like hurricane risk, environmental regulations, and seasonal demand spikes that could impact business performance and insurance costs. A business that might thrive elsewhere could face unique challenges or opportunities in the Keys.

Conduct Thorough Due Diligence

Once you’ve identified a potential target, conduct rigorous due diligence tailored to the Monroe County area. Review financial records, lease agreements (waterfront or tourist locations often have special conditions), permits, and licenses required by local authorities. Pay special attention to how local regulations, FEMA flood zones, and redevelopment restrictions may affect operations or future growth. Engage local advisors who understand these complexities to avoid costly surprises.

Engage With the Community

Success in Monroe County often depends on strong community ties. Before finalizing your purchase, take the time to meet with local business owners, tourism associations, and relevant government officials. Building relationships can help you understand local consumer preferences, staffing solutions, and effective marketing channels. Additionally, a visible and involved owner can boost your reputation and help attract both locals and tourists to your new venture.