regex101: Python Match Workspace

Regular Expression

(?<!\S)(?=([^<>.\]]*[Vv]acation\b))\1(?:[,'`´() \\]+\w+){0,200}\s*[Mm]aledives\b[^<.\]]*

New

> Man i love vacation. I should go to the Maledives. Actually i´ll book a vacation to the Maledives now. <


Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive Actually i´ll book a vacation to the Maledive

> Man i love vacation. I should go to the Maledives. Actually i´ll book a vacation this is a test before the match with a lot of words to the Maledives now. <

> Man i love vacation. I should go to the Maledives. Actually i´ll book a vacation this is a test before the match with a lot of words this is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsto the Maledive now. <


> Man i love vacation. I should go to the Maledives. Actually i´ll book a vacation this is a test before the match with a lot of words this is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsthis is a test before the match with a lot of wordsto the Maledives now. <


Actually i´ll book a vacation to the Maledive now. Actually i´ll book a vacation to the Maledive now. Actually i´ll book a vacation to the Maledive now. Actually i´ll book a vacation to the Maledives now.
Actually i´ll book a vacation now.