Christopher Powell est en Malaisie avec sa fiancée et son père pour capturer des animaux sauvages. Pendant une chasse, il est attaqué par un tigre et ses guides s'enfuient le laissant pour mort. Mais le tigre est le compagnon d'Hula, une belle jeune femme qui a grandi par elle-même dans la jungle. Elle sauve Chris et le ramène dans la grotte où elle vit. Tout en le soignant, elle va tomber amoureuse de lui. Guéri, il revient à son campement avec Hula qui a suivi. Mais leur arrivée ne fait pas que des heureux, Ava est jalouse de la complicité entre Hula et son fiancé et les indigènes voient d’un mauvais œil la présence du tigre et de son amie, ce qui va causer bien des problèmes.
In an Indian village, Buldeo, an elderly storyteller, is paid by a visiting British memsahib to tell a story of his youth. He speaks of the animals of the jungle, and of the ever-present threats to human life posed by the jungle itself. He then recalls his early life:
Mowgli's village is attacked by the vicious tiger Shere Khan (voiced by Sherman Howard) and he gets lost in the ruckus and runs into the jungle. There, Mowgli met Baloo the wise bear (voiced by Brian Doyle-Murray), Bagheera the black panther (voiced by Eartha Kitt), and the rest of his animal friends and they have adventure after adventure. Towards the end, Mowgli sees humans, but decides to stay away from them and live with Baloo, Bagheera, and the rest of his friends in the jungle.
Toomai (Sabu), a young boy growing up in India, longs to become a hunter. In the meantime, he helps his mahout (elephant driver) father with Kala Nag, a large elephant that has been in their family for four generations.
During the fall, Tigger has been bouncing on anyone he comes across for fun, especially Rabbit when he is gardening, which angers Rabbit, so he calls a meeting with Pooh and Piglet and formulates a plan to prevent Tigger from bouncing abandon Tigger in the woods, and find him the next day so hopefully Tigger will stop bouncing on his friends unexpectedly. Initially the plan seems to work, but when Rabbit, Pooh, and Piglet cannot find their way home, Pooh makes a suggestion about following a sandpit in order to find their way out of the forest. In an attempt to prove Pooh wrong, Rabbit wanders away. Pooh and Piglet then fall asleep, but are woken by Pooh's empty stomach. He explains to Piglet that his honeypots have been calling to his tummy from home and that he couldn't hear them over Rabbit's voice. Pooh and Piglet find their way out of the forest, but are immediately bounced by Tigger. Piglet, realizing that the plan failed, mentions Rabbit's plan, and Tigger goes into the forest to find him. Rabbit walks through the forest by himself, and is scared by numerous noises such as a caterpillar eating a leaf and frogs croaking. Rabbit tries to run away in a panic, only to be tackled by Tigger. Rabbit is humiliated that his plan to lose Tigger had failed. Tigger explains to him that "Tiggers never get lost", and takes Rabbit home.
The film's content is derived from three previously released animated featurettes Disney produced based upon the Winnie-the-Pooh books by A. A. Milne: Winnie the Pooh and the Honey Tree (1966), Winnie the Pooh and the Blustery Day (1968), and Winnie the Pooh and Tigger Too (1974). Extra material used to link the three featurettes together was added to allow the stories to merge into each other.
Two days before Christmas, Christopher Robin writes out a letter to Santa Claus for him and his friends in the Hundred Acre Wood, asking for the following presents:
On a remote island, a Primal Park security guard enters a locked restricted area, where a sabre-tooth cat kills him. As Alan performs an inspection, Niles takes his ex-brother-in-law Grant and Autumn to a hotel where other investors are waiting. Security guards Savannah and Sundip ignore an alert on a gate, but Alan insists on checking it. College students Kirk, Alaina, Robbie, Alys, and Collette arrive to complete a scavenger hunt, and Niles takes them to the hotel.
Enfant, Mowgli est élevé par une meute de loups au cœur de la jungle indienne. Tandis qu'il apprend les lois souvent âpres de la jungle, sous la responsabilité de l'ours Baloo et de la panthère Bagheera, Mowgli est accepté par les animaux de la jungle comme l'un des leurs – sauf par le terrible tigre Shere Khan. Mais des dangers bien plus redoutables guettent notre héros, au moment où il doit affronter ses origines humaines.