Dateline Washington — During his strenuous race for governor of Virginia in 2005, Timothy M. Kaine found himself chatting with James Murray, a wealthy venture capitalist, and acknowledged that the physical strain of the campaign was becoming difficult.

In response, Mr. Murray made an offer: Win or lose, after the November election, Mr. Kaine and his family should spend time at Mr. Murray’s vacation home on the exclusive Caribbean island of Mustique. The home, situated on an island point with stunning views of the Caribbean and Atlantic oceans, would be empty and Mr. Kaine could use it for free. “No sleeves off my vest,” Mr. Murray recalled in an interview.

Mr. Kaine disclosed that gift in his annual Virginia financial disclosure form, estimating that the free use of the home came at an $18,000 value.

Such gifts were legal at the time in Virginia, which had permissive laws that allowed officeholders to accept gifts of any amount provided those valued at more than $50 were disclosed.

But Republicans have signaled in recent days that they will use Mr. Kaine’s acceptance of that and other freebies as a line of attack against the newly selected vice presidential candidate, looking to stoke concern among Democrats that Mr. Kaine is not the progressive candidate they had hoped for.

“He followed the rules, but it’s a question of whether the Democrat Party can stomach that coziness with donors,” said former attorney general Jerry Kilgore, the Republican whom Mr. Kaine defeated in 2005. “Their base, at this point, is anti-corporate America, anti-what these gifts stand for: access and influence.”

Who Noticed – or Cared?

Such gifts drew little attention in Virginia until Mr. Kaine’s successor, Gov. Robert F. McDonnell, was convicted of federal corruption charges in 2014, accused of accepting gifts and sweetheart loans from a dietary supplement executive in exchange for promoting the businessman’s company.

The Supreme Court in June overturned Mr. McDonnell’s conviction, finding that authorities had incorrectly instructed the jury about how to define an illegal quid pro quo. Mr. McDonnell has maintained he did nothing for businessman Jonnie R. Williams Sr. in exchange for his gifts. Prosecutors are weighing whether to attempt to retry Mr. McDonnell and his wife, Maureen, who was convicted alongside him.

There are stark differences between Mr. Kaine’s gifts and Mr. McDonnell’s. For one, Mr. Kaine’s gifts were properly disclosed. Mr. McDonnell failed to disclose some of what he received.

For another, Mr. Kaine never has faced accusations of promising state action in exchange for any of his gifts.

“During his eight years as lieutenant governor and governor, Sen. Kaine went beyond the requirements of Virginia law, promptly disclosing any and all gifts received, including those beneath the reporting threshold,” said Kaine spokeswoman Amy Dudley. “All disclosure information — the vast majority of which was for work-related travel expenses rather than gifts — has been publicly available for years and never once raised any concerns of impropriety.”

During his eight years as Virginia’s lieutenant governor and then governor, Mr. Kaine disclosed that he accepted $201,600 in personal gifts, according to data compiled from the Virginia Public Access Project, a nonpartisan tracker of money in state politics.

The majority of those gifts came in the form of air travel, including from the 2008 campaign of President Obama, which paid to fly Mr. Kaine across the country as a campaign surrogate. Under murky Virginia law, the proper way to disclose such political travel has been unclear. Other politicians have disclosed it as a campaign contribution to their political action committee, rather than a personal gift, as did Mr. Kaine.

More than $32,000 of Mr. Kaine’s gifts were travel expenses paid by the state’s economic development agency during trade missions he took in his official role as governor.

Old Friends

Some of Mr. Kaine’s other gifts were more tangible. Stuart C. Siegel, chairman of S&K Famous Brands Menswear, gave Mr. Kaine a total of $5,500 in clothing in 2003 and 2005. Mr. Siegel is a close friend of Mr. Kaine.

Mr. Kaine introduced Mr. Siegel to his wife and presided at their wedding. Mr. Siegel did not return a call for comment.

In 2006, Teva Pharmaceuticals paid $12,000 to fly Mr. Kaine to the annual meeting of the Democratic Governors Assn. Two years later, the company received a $900,000 economic incentive to expand its Virginia operations. The company has donated to campaigns of both Democrats and Republicans in Virginia.

Other gifts Mr. Kaine reported included $850 worth of Washington Wizards basketball tickets from a Virginia businessman who had contributed $10,000 to Mr. Kaine’s 2005 campaign; eight tickets to a Dave Matthews concert from the University of Virginia; and a 3-by-5-foot prayer rug from then-Afghan president Hamid Karzai.

In an interview, Mr. Murray, who had contributed $41,000 to Mr. Kaine’s campaigns for governor and lieutenant governor, said he believes Mr. Kaine’s office likely overvalued the cost of a week’s stay in his vacation home. The vacation was the single largest gift Mr. Kaine reported in his eight years as a state official. Mr. Murray noted that Mr. Kaine and his family paid for their airfare, as well as meals and other expenses during the trip.

Mr. Murray, who had been business partners for years with Mr. Kaine’s predecessor, Mark R. Warner, had served under Mr. Warner on an unpaid state committee that helps vet possible candidates for appointment to boards of public colleges and universities. He was reappointed to the position by Mr. Kaine, with whom he was also friendly. But Mr. Murray insisted that there was nothing he would have wanted in return from the new governor when he offered the use of his home.

“I’m happy to talk about this — I do think the public has a right to know,” he said. But, he added, “I’ve got no business with the government of Virginia, and I’ve never gotten anything in return.”

In a 2013 op-ed in The Washington Post, published as the state reeled from revelations about Mr. McDonnell, Mr. Kaine wrote that he had received gifts and “duly reported” them while in state office. But he said he saw the benefits of the federal system, which imposes far more restrictions, and he advocated adopting a similar system at the state level.

“Virginia’s wide-open rule is justified by a smug attitude: We can trust ourselves to do the right thing, and transparency is all that is needed to keep the system honest,” he wrote. “Gifts to elected officials can create a subconscious sense of gratitude in even the most upright public servants. And the public probably will perceive such gifts as creating improper influence, whether or not that happens.”

The Virginia General Assembly did ultimately change the state law, prohibiting elected officials from accepting gifts of more than $100 from lobbyists and others with business before the state.

Ms. Helderman is a political enterprise and investigations reporter for The Washington Post, where this article was first published.

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