Ben and his friend, Jack Marshall, win a four-day stay at a private Miami, Florida, resort. Sitting down at the poolside bar, they are accosted by the head of hotel security, who informs them that the party is for guests only, but Jack shows his room key, and the embarrassed security head slinks away. The next day, “The Maestro” talks on the phone with his employer as he keeps an eye on Mrs. Amanda Rawlings, an older woman wearing the diamond necklace he has been commissioned to steal. As Ben ogles all the bikini-glad girls around the pool, he accidentally bumps into Patti, a waitress. Scott, the wait staff manager, intervenes, chastising Patti for consorting with guests. Ben apologizes, and when he walks away Scott asks Patti to join him after she gets off for the evening. Without much enthusiasm, she tells him, “We’ll see.” Jack catches a young boy named Georgie trying to snatch the bathing suit off Bobbie Sue, The Maestro’s wife. He throws Georgie into the pool, and uses the opportunity to try to get to know Bobbie Sue. However, she brushes off Ben and Jack with practiced ease. Jack catches a break when Ben discovers Bobbie Sue dropped her hotel key. Convinced that she did so on purpose, Jack persuades Ben to join him as he heads toward her room. Once there, Jack strips naked. When there is a knock on the door, he is convinced Bobbie Sue is outside, and goes to the bedroom, leaving Ben to open the door. It is not Bobbie Sue, but The Maestro out in the hallway. The Maestro takes the teenager for the barber he is expecting. Before Ben can do too much damage, The Maestro receives a phone call, and tells his employer that if necessary he will kill the woman with the necklace in order to obtain it. Another knock on the door brings Bobbie Sue into the room. Ben keeps his face hidden long enough for her to go to the bedroom. She discovers Jack hiding in the bedroom closet and hides the boy when her husband enters to get money to tip the “barber.” However, when The Maestro discovers the damage done to his hair, Ben and Jack escape just by the skin of their teeth and hide out in the ladies’ exercise room. When the Maestro follows them into the exercise room, he runs afoul of the aerobics instructor, who throws him out. Ben and Jack make their way to the pool deck where Patti takes their drinks orders. Jack leaves to give his friend a clear path with Patti, but before they can get better acquainted, The Maestro and Bobbie Sue arrive, and Ben drags Patti under the table to avoid being seen. After they pass, Ben asks Patti for a date, and she agrees. However, their conversation is broken up when Scott interrupts them and sends Patti back to work. Jack becomes smitten when he sees Dana Rawlings in the pool. A waiter tells Dana he must first win the approval of her grandmother, Mrs. Rawlings. Jack bribes the waiter to page him by the name “Dr. Marshall” in order to get Mrs. Rawlings’s attention. Mrs. Rawlings suggests that Dana go out with the “doctor” that evening, along with her other granddaughter, Dana’s cousin, Shirley. Jack asks if he can bring a friend, and Dana likes the idea. A reluctant Ben joins him on the double date. Shirley turns out to be on a spiritual journey as a follower of guru Baba Rama Nana, and prefers to be called Halli Zumba. Shirley/Halli wants to stay in, and Jack leaves Ben behind to keep her company, and also gives Ben some Quaaludes to help Shirley “loosen up.” In the hotel cocktail lounge, The Maestro enters wearing a white Western-cut suit and a cowboy hat. He introduces himself to Amanda Rawlings as “Igor Kaminski Repulski” and asks her to dance. As he attempts to unlatch her necklace, Mrs. Rawlings knocks off “Repulski’s” hat. Repulsed by the botched haircut underneath, Mrs. Rawlings beats a hasty retreat. In the Rawlings hotel room, Ben, now called Raga Lala, is given a lesson in spiritual chanting by Shirley/Halli to cure a feigned headache. When he claims his headache is cured, Shirley/Halli strips and urges Ben/Raga Lala to “be free” with her. She opens the curtain on a portrait of Baba Rama Nana, and goes into a fit of ecstasy, but when Ben attempts to hug her, she shrieks, “Flesh cannot touch flesh in the master’s presence,” and pulls away from him. She leaves him in the room, facing the painting of Baba Rama Nana chanting, “Come to me,” as she promises to return. A little worse for the wear, Mrs. Rawlings comes back with a headache. She freaks out seeing Ben wearing nothing but a turban, and chases him from the room. She spots the Quaaludes on the coffee table and, thinking they are aspirin, takes four tablets. Ben races around the hall using the turban to cover his genitals. He hides under a room service cart tablecloth, only to be wheeled into The Maestro’s room. Upset that his rotten haircut caused him to lose the chance to grab Mrs. Rawlings’s necklace, The Maestro threatens to kill the barber when he sees him. Bobbie Sue suggests he take a hot bath and she will come in to play “pick a boobie.” Ben sees his chance to escape, but the hotel security officer is in the hallway. He makes his way to the bathroom and climbs into the tub. The Maestro, his eyes covered with suds, believes Ben to be Bobbie Sue and pulls the boy toward him, but Ben beats a hasty retreat, chased by The Maestro. Ben escapes to his room. Patti waits for Ben in front of the hotel, but when he does not arrive, she agrees to let Scott drive her home. Ben arrives just in time to see them drive away. Meanwhile, the real hotel barber goes to his car, opens the trunk, and puts on a military uniform. The Quaalude-besotted Mrs. Rawlings accosts him, and drags the barber into the bushes. Back at the poolside bar, Ben and Jack sit next to a guest named Curt. His girl friend chastises Curt for chasing other women, and threatens to retaliate by picking up the first man she bumps into. Jack asks Ben to stall the imposing Curt, while he makes sure to be the first man Curt’s girl friend meets. Jack finds Curt’s girl friend, but she refuses to go back to Curt’s room for fear he will discover them in bed together. At the bar, Curt takes Ben into his confidence about his amorous intentions with his new girl. Afraid Curt will discover Jack, Ben switches keys with Curt, who asks Ben to escort the blonde to the room he and Jack share while he does a couple of things. When Ben gets to the room with Curt’s date, she goes to the bathroom. He hears Jack and Curt’s other girl friend in the bedroom, where she has become ill before she and Jack can make love. Ben and Jack try to keep the two women from meeting, but ultimately fail. Thinking they have set him up, Curt chases after Ben and Jack. The following day, Patti sees Ben leaving the resort and asks why he did not meet her the night before. He tells her he was there and saw her leaving with Scott, and she responds that he was a half hour late and she needed a ride home. Scott arrives and tells Patti to get back to work. When she hesitates, he drags her away and Ben comes to her rescue. Ben gets beaten up, and Patti gives him a thank-you kiss for his chivalry. The Maestro knocks on Mrs. Rawlings’s hotel room door, this time dressed in yachting clothes and a captain’s hat. Believing he has come for a tryst, Mrs. Rawlings tries to let him down easy, but he is only after her diamond, and she fends him off with karate, and sends him plummeting over her balcony railing. As she calls hotel security, The Maestro climbs back up and pulls a pistol on her. Back in their hotel room, Ben exercises as Jack and Dana Rawlings get up for the day. As Dana goes to the bathroom, Patti arrives with a room service order. When Dana comes out of the bathroom, Patti thinks she is with Ben and leaves. As Ben attempts to explain, he is recognized by the Maestro, who gives chase. Ben run into a dressing room where models are getting ready for an afternoon fashion show. He dons a dress and lady’s hat, in his effort to elude The Maestro. Mistaking him for a her, The Maestro tries to romance the costumed boy. He pursues Ben into an elevator, but Curt also enters. Curt also becomes enamored of the veiled “lady,” and starts feeling “her” up. The Maestro pulls his pistol and shoves Curt out of the elevator, then tries to tempt Ben with the Rawlings diamond. He accidentally drops the diamond down the front of Ben’s dress, and when he tries to recover it, The Maestro finally recognizes Ben as the rotten “barber.” Chaos erupts, and in the ensuing chase Shirley/Halli returns to her room to give an offering to the portrait of Baba Rama Nana. She hears her grandmother, who has been tied up by The Maestro and shoved into the closet, and believes the guru is speaking to her. Ben runs back to the women’s locker room, screaming that he/she is being followed by a man. The aerobics instructor and the young women beat The Maestro and the hotel security officer and drive them from the locker room. Scott chases Ben through the hotel kitchen, but this time Ben gets the better of his rival. In the hotel terrace restaurant, The Maestro catches up with Ben and Jack and opens fire with his pistol. He runs out of ammunition, pulls out a sub-machine gun, and continues shooting. Patti is in the line of fire, and Ben attempts to draw The Maestro’s aim, but falls to the floor from the restaurant balcony. As The Maestro demands the diamond, the head of hotel security arrives to congratulate him for capturing the “criminals.” However, when he slaps The Maestro on the back, the diamond thief’s back goes out and he doubles over in pain. Mrs. Rawlings arrives to sort out the confusion, and afterward Ben, Jack, Patti, Dana, and Mrs. Rawlings prepare to set off on another vacation to Jamaica.