When President Obama and his family arrives for a two-week stay this weekend, it will mark the 10th time in the past 20 years that the Vineyard has hosted a summer White House.

Over the years, since the Clinton family’s first visit in 1993, First Families have stayed at sprawling south shore farms and at cozy Chilmark enclaves. They have been treated to views of the Atlantic and of Vineyard Sound. They have ridden horses and played basketball.

In many ways, a summer White House is the same as any other summer house. It’s a place to get away, kick back and savor the season. And for the people who host presidential families, leaving their home for a week or two is akin to preparing any summer home for visitors. Be sure the place is in good order before you leave and don’t forget to leave the door unlocked.

In many other ways, it is different.

“It’s hard to envision what it’s going to be like before it happens because it’s progressive,” said Richard L. Friedman in a telephone conversation Wednesday. Mr. Friedman’s Oyster Watcha home, which was formerly a working farm, was home to the Clintons in 1994, 1997, 1998 and 1999 (they vacationed in Jackson Hole, Wyo., in 1995 and 1996). Bill Clinton and Mr. Friedman knew each other from President Clinton’s tenure as governor of Arkansas, and Mr. Friedman extended an invitation for the family to stay on the property.

“It’s a fantastic property with incredible privacy and a very classic New England kind of feel to it,” Mr. Friedman said. The views are spectacular, he added: “It’s just magical.”

In 1993, Clintons stayed at home of Robert McNamara. — Mark Lovewell

Prior to the family’s arrival, Secret Service agents paid several low-key visits to the home, Mr. Friedman recalled.

“A lot of [security] stuff comes in, and then it tapers off,” he said. “It’s a scene.”

He praised the professionalism of the Secret Service, calling their efforts “remarkable.” He made just one request of the team — that they not put any holes in the walls of the home, a restored farmhouse.

“When they left, they put everything back, exactly,” Mr. Friedman said. “They must have a little map — the mustard goes here — or something.”

Mr. Friedman said there was little he had to do to prepare for the visits.

“The Clintons are quite easy to please; they’re not demanding people,” he said. “There’s a wonderful kitchen there with a big harvest table, and they would eat at the table and they would read books and play Scrabble.” The family brought a large stock of books on vacation, and made frequent trips to Bunch of Grapes. The bookstore is now a favorite Obama family stop as well.

During the Clintons’ first Vineyard visit they stayed at the two-bedroom guest house owned by the late Robert S. McNamara, former Secretary of Defense under Presidents Kennedy and Johnson. Security and White House officials stayed in the five-bedroom main house.

“A low-profile summer home,” according to a Gazette story written at the time, the residence was a typical Vineyard construction — weathered cedar shingles, southern orientation.

Hammock at Blue Heron farm, fit for a presidential nap. — Mark Lovewell

In a 1993 Gazette interview, architect Benjamin Moore, who designed Mr. McNamara’s house and guest house, offered his perspective on why the home was such an ideal retreat.

“The beaches, the privacy, the quiet,” he said. “The peacefulness, which is why the Vineyard is so important to people, particularly people who are in positions of responsibility. This place is such a contrast to what their lives are. It’s a place to think, or not to think,” he added.

“I think, you know, having a place where they can really be isolated and not under surveillance [was important],” Mr. Friedman said.

The same considerations were taken when President Obama and his family prepared their visits. Securing a place to stay was handled through Wallace and Co. Sotheby’s International Realty, who also helped coordinate the Clinton visits.

Tom Wallace, a company partner and owner, said he remembered sitting down and drawing up a map of potential locations.

“We went on to say, here are some corridors that have easier access coming and going,” he said. “We made recommendations based on what would be user friendly from the First Family’s point of view.” Downtown Edgartown was quickly ruled out, he said. Chappy would be too cumbersome, East Chop too exposed.

But Chilmark was just right. For the first three summers, the Obamas stayed at Blue Heron Farm, a family compound on the Tisbury Great Pond.

“Multiple buildings could be used for the Secret Service, White House staff, medical officers, and the First Family themselves,” Mr. Wallace said. The farm was sold in 2012, and last year a new rental location was found, at the home of David and Patty Schulte.

Mr. Schulte, who is from Chicago and was previously acquainted with the Obama family, said that he had never considered renting his house before Wallace and Co. first asked about the possibility.

“We did very little,” Mr. Schulte said. “The White House and their staff and the Secret Service have done this many times in many places.” Similar to Mr. Friedman’s experience, Mr. Schulte said that when he and his wife returned to their home last year, there was no sign any tenants had been there at all — not even Bo Obama.

“We have two dogs,” Mr. Schulte said. “It was fine with us for the president to bring Bo.” The home where the Obamas will stay this summer is also dog-friendly. Joanne Hubschman, who is renting her home off of North Road to the family, owns a Portuguese water dog.

The Obama family has been “wonderfully open to different settings, different styles of homes, and different amenities at the places they’ve stayed,” Mr. Wallace said.

The Schulte home prompted some controversy when a portion of South Road was closed to vehicle traffic during the presidential visit because of security concerns. That decision was made well into the planning stages; when the Schulte property was first proposed as a location, there wasn’t an expectation of needing to close the road.

Mr. Wallace said he did hear from a number of people who had little problem with the closure.

“I got many compliments from cyclists about having a designated bicycle path on South Road,” he said. North Road will remain fully open during the upcoming visit.

Preparations for this year’s visit have gone smoothly, Mr. Wallace said.

“The collective efforts that everyone makes to work together to make it all look easy is really fun to see,” he said.

“I loved it,” Mr. Friedman said of his hosting experience. “I have no regrets, and I have huge affection for the Clintons and what they’re doing and what they did.” He said he also appreciated being welcome on his property if he wanted to stop by

Though they received “boatloads of publicity,” about their home after last summer, the Schultes have not rented it since. They received a hand-written thank you note from the Obamas, which they framed together with official White House photographs of the First Family at Snail Road.

“We got a kick out of it,” Mr. Schulte said. “We’re flattered, we’re honored. It’s a nice house, we think.”